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Scenic Roads of Redding, Connecticut

Redding's Scenic Road Ordinance was adopted and became effective in January 1986, the first in the region. Since that time sixteen local roads have received Scenic Road designation. These scenic and rural roads extend for over 18 miles throughout the town and typify Redding's picturesque charm and character.

In the words of John Mitchell, author of the 1984 Open Space Plan, they are:

"pieces of the frame we call our country atmosphere.
We must find a way to preserve them."

If you would like additional information about the Town's Scenic Road ordinance please visit: ScenicRoadOrdandWalls.pdf for the full text of the Scenic Road Ordinance and Stone Wall Addendum.

Cross Highway: From Hill Road (Rt. 107) to approximately 700 feet easterly of Newtown Turnpike; Boy's Club property line. Length in miles of scenic section: 1.9 miles. Date approved: 8 Apr 1997. Scenic Features: Hills and valley, meadows, mature trees, historic buildings, distant views.

John Read Road: From Lonetown Road (Rt. 107) to Black Rock Tpk.(Rt.58). Length in miles of scenic section: 1.08 (entire road). Date approved: 22 May 1990. Scenic Features: Upland terrain, meadows, stone walls, woodland, dirt road.

Lee Lane: From Redding Road (Rt. 107) to end. Length in miles of scenic section: .32 (entire road). Date approved: 10 May 1988. Scenic Features: Gentle terrain, mature trees, narrow winding road.

Limekiln Road: From Redding Road (Rt. 53) to Lonetown Road. Length in miles of scenic section: 1.7 (entire road). Date approved: 10 May 1988. Scenic Features: Valley to rugged upland, woodland, distant views, winding road.

Marchant Road: From Simpaug Turnpike to Umpawaug Road. Length in miles of scenic section: 1.8 (entire road). Date approved: 9 Aug 1988. Scenic Features: gentle terrain, meadows, stone walls, mature trees.

Mark Twain Lane: From Diamond Hill Road to end. Length in miles of scenic section: .25 (entire road). Date approved: 22 Oct 1996. Scenic Features: upland slope, stone walls, meadows, mature trees narrow road.

Old Hattertown Road: From Poverty Hollow Road to Newtown Town Line. Length in miles of scenic section: .43 (entire road). Date approved: 22 Mar 1988. Scenic Features: broad valley, meadows, woods, winding dirt road

Pine Tree Road: From Black Rock Turnpike (Rt. 58) to Easton Town Line. Length in miles of scenic section: .65 (entire road). Date approved: 8 Aug 1997. Scenic Features: narrow stream valley, rushing brook, wooded hillsides, narrow road.

Poverty Hollow Road: From 500 feet south of Stepney Road intersection to Newtown Town Line. Length in miles of scenic section: 1.94. Date approved: 12 Sep 1989. Scenic Features: valley terrain, rushing stream, ponds, waterfalls, meadow forest.

Sherman Turnpike: From Newtown Turnpike to Sanfordtown Road. Length in miles of scenic section: 1.0 (entire road). Date approved: 10 May 1988. Scenic Features: valley to hilltop, steep hillsides, woodland, narrow partly-dirt road.

Side Cut Road: From Simpaug Turnpike and Long Ridge Road to Redding Road (Rt. 53). Length in miles of scenic section: .67 (entire road). Date approved: 13 May 1997. Scenic Features: broad valley, mature trees, stream.

Station Road: From Umpawaug Road to Side Cut Road. Length in miles of scenic section: .44 (entire road). Date approved: 10 Mar 2009. Scenic Features: gentle terrain, stone walls, woodland, stream, mature trees, narrow.

Topstone Road: From Chestnut Woods Road to Umpawaug Road. Length in miles of scenic section: .96. Date approved: 26 Aug 1986. Scenic Features: rolling terrain, woodland, meadows, mature trees, dirt road.

Umpawaug Road: From Redding Road (Rt. 107) to Redding Road (Rt. 53). Length in miles of scenic section: 3.5 (entire road). Date approved: 22 Jan 2002. Scenic Features: steep hillsides, hilltop, upland terrain, woodland, winding road.

Wayside Lane: From Redding Road (Rt. 107) to fork and thence on both branches to Umpawaug Road. Length in miles of scenic section: .82 (entire road). Date approved: 10 May 1988. Scenic Features: ledgy terrain, woodland, stone walls, narrow winding roads.

Whortleberry Road: From Gallows Hill Road to Limekiln Road. Length in miles of scenic section: .80 (entire road). Date approved: 25 Nov 1986. Scenic Features: ledgy upland terrain, woodland, narrow winding partly-dirt road.


A special thank you to Jerry Sarnelli for forwarding this updated material!

I promise to add photos in the near future.


"The Roads of Easton and Redding: Their Origins" by Daniel Cruson

Understanding the development of towns such as Easton and Redding, as well as understanding the modern interactions between areas within these towns and between the towns themselves, can only occur when the pattern of roads which govern this development and these interactions is known and understood. In any town, the road pattern is usually determined as the town is first settled. This pattern will then be modified as the town grows but through all of its modifications the basic pattern of roads which emerges with the first settlers remains. Even today, after paving, widening and cutting through new roads to give access to old farm property for subdivisional housing, the basic patterns established by the crude roadways which were first cut through the wilderness of northem Fairfield can be seen by simply glancing a map of Easton and Redding provided one knows a little of the background of this early road development.

To understand the basic pattem of roads in the Easton-Redding area it is first necessary to go back and consider the way in which the land that would later become these towns was acquired, divided among Fairfield's proprietor's, and then settled. The land that became Easton, Weston, and the southern half of Redding was formally purchased from the local Indians on January 19,1671 for "36 pounds sterling of cloth valued at 10 shillings a yard" (i.e. 72 yards of cloth.) Fairfield had already secured possession of the coastal lands from Black Rock harbor to the Saugatuck River in what is today Westport, and extending six miles inland. The Northern Purchase of 1671 , then, gave the town possession of another six miles further inland so that the town now extended from the coast northwesterly to an east-west line that coincides with modern Cross Highway in Redding.

With a weeks of its purchase, this northem land was divided among the town's proprietors. This reflected a strong desire on the part of the town to get all common lands into private hands quickly and thereby strengthen the town's claims of ownership over the potential claims of other local Indians who may have felt entitled to land in this area. In fact, the Indian John Wampus in 1671 did step forward and try to claim a substantial parcel of land in Aspetuck. He claimed this land was his by right of his marriage to the daughter of Romanock, the chief sachem of the Aspetuck Indians, from whom she inherited the title of the land at his death ten years before. After a long and very involved period of legal maneuvering, the courts awarded the land to the proprietors to whom it had been distributed for they were in possession of the land and living on it, whereas Wampus had never actually taken possession of it.

The proprietors of Fairfield were those people who were either the first settlers of the town or descendants of the first settlers who were entitled to take ownership of a share of common land as it was divided. A problem accompanied the division was the land to be equitably divided? This did not mean that each proprietor was to receive an equal amount of land, for Proprietors were not equals. Some were far wealthier and, by the later half of the 17th century owned more land than others. To these wealthy Proprietors would go the largest parcels of land. The problem, rather, was to insure that regardless of its size, no individual would be left with land of poor quality for farming while another proprietor would end up with fertile productive land, in addition, the division must insure against one proprietor receiving land that was tucked into quality for farming while another proprietor would end up with fertile productive land. In addition, the division must insure against one proprietor receiving land that was tucked into a remote northern region while another received land that was readily accessible in the southem portion of the purchase.

The answer to these distributional problems was the "long lot". Town officials first began carving up the Northern Purchase by setting off a strip of land 1/2 mile wide and which ran across the town from East to West about two miles above the village of Fairfield. Perpendicular to this Half Mile Common another strip of land was set off which was one mile wide and which ran from what is today the green in the center of Redding, south to the Half Mile Common. This  was appropriately called Mile Common. To either side of the Mile Common long lots were laid out. These lots were long, thin stripes of land that ran from the Half Mile Common nine mile north to the towns northern boundary. They varied in width from 50 to over 850 feet, the widest lots being given to the wealthiest and thus more deserving proprietors. Although their width varied considerably, most of these lots averaged about 490 acres.

The long lots were not immediately settled but rather were held for speculation, either hoping that the land would increase in value in the future or that it could be given to the proprietor's sons so that when they came of age they could establish farms of their own. Land records indicate that these lots were also frequently sold or traded between proprietors. Regardless, historians such as Thomas Farnham who have extensively studied this area, doubt that there was any settlement on these lots before 1725. This did not mean that the proprietors completely ignored their holdings to the north, for as soon as land division is made, concern was expressed over access to the northern properties and plans for roads were drawn up.

A year after the 1671 land division a highway was laid out running East and West of the Half Mile Common. This road assured owners that they could gain access to the bottom or southern portion of their long lot. This road survives and is appropriately called Long Lots Rd. in Westport. Looking at a modern map of the Westport-Fairfield area, it is easy to see that Long Lots Rd. forms a straight line east to west, and that Hulls Farm Rd. and Fairfield Woods Rd. form eastern extensions of this line. All three of these roads along with several other shorter ones were at one time connected and formed the northern boundary between the Half Mile Common and the southern terminus of the long lots.

Marking boundaries with roads was a common colonial practice. Modern Park Ave., which used to be called Division St. or Line Highway, is the remnant of such a boundary road marking the line between Stratford and Fairfield after the exact boundary had been finally worked out in the 1690's. This road was originally a six rod road meaning that the right of way for the road was six rods or 99 feet wide (one rod=l6.5 feet). It begins as it does today in eastern Redding, where modern Stepney Rd. intersects with it and proceeds south in as straight a line as topological features will allow, through the campus of the University of Bridgeport, ending at the monumental arch which marks the entrance to Seaside Park. One stretch of the road was probably never completed and that ran from the intersection with Flat Rock Rd. in Easton south, to a point just south of the Merit Parkway bridge. This part of the straight line route is a very narrow part of the Mill River valley which was formerly known as a wilderness and scenic area called Nick's Hole. There was a narrow dirt road that ran up this through this valley and which has become part of the modern Park Ave., but this road twisted and turned following the contours of the valley and not running in a nice straight line as a good boundary road should. (The section of road between Flat Rock Rd. and the southern end of North Park Ave. in Easton was destroyed by the Easton Reservoir.)

The northern boundary of the town of Fairfield was also marked by a boundary road which is still an important east-west corridor for Redding. This road consisted of the modern Church Hill Rd., Cross Highway, Great Pasture Rd., Fox Run Rd., and Seventy Acres Rd. Looking at a modem map of Redding, it can easily be seen that these roads form an almost straight line which bisects the town from east to west. One section of the boundary road, east of Fox Run Rd. was obliterated when Mark Twain built his residence, Stormfield, on it and other sections twist and turn to negotiate the steep hills which characterize any east west road in this area, but on the whole the route is straight and direct, making a clear delineation between the northern long lots and the area to the north which originally was not claimed by any of the surrounding towns, hence known as the Peculiar.

Once the boundary roads were established, thoughts turned to the need of gaining access to the interior and northern portions of the long lot themselves. To meet this need the "upright highways" were laid out starting in 1692. These roads derived their name from the fact that they ran in an upright or north-south direction. In fact, they ran slightly to the northwest or to the 11 o'clock position on an imaginary clock face so they were also known as "11 o'clock roads." One stretch of road in Weston is still called by that name. The upright highways were to run between the long lots giving owners access to the northern portions of their lots. As a result it became common to refer to the highways by the name of the adjacent long lot owner. Modern roads such as Burr St, Morehouse Highway, and Tumey Rd. are quaint relics of this practice.

Like the boundary roads, the upright highways ran in a perfectly straight line except where geographical features made this impossible. Sport Hill Rd., for example, runs through Easton in a straight line except where it deviates to get around Beacon Hill, where Silverman's orchard has been establish (just north of the Easton firehouse). The straightness of these roads derives from the fact that they were laid out between perfectly straight long lots which in turn were laid out on paper, regardless of geographical features, before they were laid out in fact.

Unlike the boundary roads, few of the upright highways were ever completely finished. Of the four upright highways that pass through Easton into southern Redding, only Sport Hill Rd., formerly called Jackson's Highway, was substantially completed, even though it ended, as it still does, at a rock outcropping on Stepney Rd. about one mile short of the cross highway boundary road in Redding. As with many of these early roads, rough terrain north of this point simply made it impractical to push the highway further. It was far easier to turn to the west and go up the valley. When geographical obstacles appeared, our colonial forebearers, like their descendants today, often took the path of least resistance.

Another relatively complete upright highway is Morehouse Highway. Although a bypass has been constructed just where the road enters Easton, the old road, complete with its hairpin tums which enabled the traveler to get to the top of the 90 foot high hill, can still be seen extending north off of Congress St. across from the Fairfield branch of this road. From the top of the hill the old upright highway proceeds in the characterisric straight line fashion, northward across Center Rd., stopping at Westport Rd. (Rt.#136). At one time the road extended further crossing Slady's fruit farm . Now this section of road has been obliterated but it does pick up north of the farm where it becomes Bibbins Rd.. Bibbins picks up the straight northward movement to Cedar Hill Rd. At this point the paved road stops but a remnant of the old road can be seen passing into the woods north of Cedar Hill, although it appears now as only two parallel stone walls with clear ground between them. These walls stop at the base of a rock escarpment and it is doubtful if the stretch of road which was to be laid out to the immediate north of this cliff ever was. A more northern section of Morehouse Highway was laid out in Redding, however. This appears as Turney Rd. today, and it runs behind Joel Barlow High School. Up until the beginning of this century the road ran down to Rock House Rd. in Eastoh. The old route may still be followed by tracing the parallel line of stone walls as they run south of the athletic complex. The northern end of Turney Rd. is its intersection with Meeker Hill Rd., but originally it ran north to Church Hill Rd., the eastern end of the cross highway boundary road. A small portion of this northern terminus survives as Iris Lane.

From the incomplete nature of Morehouse Highway we have a clue as to the manner in which these roads were constructed. The first section of the upright highways to be laid out were the southernmost which rose perpendicular to the northern boundary of the Half Mile Common. The lines which determined the location of these first road sections were establish by a surveyor in 1692 and it is probable that the first mile or so of highway was at least cleared of trees and major obstructions. Because there was no move to settle in the long lots until the second quarter of the 18th century, however, the highways were little used after they were first laid out and they quickly reverted to the wild. Thus we find that the town had to resurvey the southern limits of the highways in 1707, 1711, and again in 1714. Only after 1738, when the town again voted "to clear the highways that run between the long lots", does mention of surveying and clearing these roads disappears from town records, implying that there was sufficient travel on them after this date to keep the roads relatively clear and the rights of way sharply defined. As Fairfield settled the interior northern lands, the roads would have been pushed farther north, until the areas which were last and lightly settled were reached and geographical obsticals were encountered, then, as with Morehouse Highway north of Bibbins, there was little motivation to push the roads further.

At the same time that the upright highways were being pushed northward, the sections of these roads that on paper rested in Redding were begun and pushed southward. Within a year of purchasing Lonetown Manor in 1714 and thereby beginning the settlement of Redding, John Read petitioned the town of Fairfield to survey the back or northern end of the long lots and with them the northern terminuses of the upright highways. It is obvious by this request that Read anticipated growth in the community which he was helping to establish. Only by determining clearly and definitely the boundaries of the northern long lots could he expect to induce settlers to either move north onto their own lots or purchase a section of the northern long lots from one of the proprietors and build a family farm on it. In fact, the narrow nature of these lots made it essential that their boundaries be established before settlement could occur because a farm could not be established on a strip of land to 200 feet wide. Thus the northern portion of neighboring long lots had to be purchased to put together a workable piece of farm land.

Settlers also could not be induced to move to the northern long lots if those lots were inaccessible. Therefore, after the 1714 survey, the northern portion of the upright highways were laid out and cleared. Thus, even though Morehouse Highway was never cleared much beyond Bibbins Rd., the northern sections, Iris Lane and Turney Rd., were.

In western Redding this process of highway construction can be seen even more clearly. To the west of Redding center, the upright highways which passed between the western long lots, (today Weston) should have continued up to the western extension of the cross highway boundary road, namely Seventy Acres and Fox Run Rds. Only two short section of upright highway, however, appear to have ever been laid out; Dorothy Rd, along with part of Wayside Lane which are the northern sections of the upright highway which survives as Bayberry Lane and White Birch Dr. in Weston, and Goodsell Rd. which was part of the highway that survives as Old Hide Rd. and North Ave. In western Redding, then, only the sections of road which were needed for convenient movement in that area of town, were constructed and even then they were never run completely north to the cross highway boundary road.

Another factor which severly hampered the construction of the western upright highways was Devil's Den. This piece of land was virtually useless except for obtaining fire wood and later in the 19th century, turning it into charcoal. The land is rocky with little soil and what soil there is tends to be infertile. Even worse, the terrain in this area is so uneven that even the pasturing of cattle is dangerous. As a result, Devil's Den has remained unused, unsable, and open space down to the present. The terrain not only removed the motovation to push the highways through this region, but it also made it nearly impossible. Therefore, the western upright highways were laid out and cleared through central Weston and there they stop. Two northern sections of highway are then constructed solely for local convenience and not to be able to pass back and forth to Fairfield village as was the original purpose of these roads.

For the sake of completeness, the remaining two upright highways in the eastern long lots should be traced since they are part of the basic road structure of Easton, as are Sport Hill Rd. and Morehouse Highway. Just west of Morehouse Highway is Wilson's Rd. or Highway. Today the road stops at Beers Rd. but originally, before the Bridgeport Hydraulic Company closed it in 1914, it continued southerly into and through Fairfield to Fairfield Woods Rd., the boundary road for the Half Mile Common. In a northerly direction Wilson's Rd. passes over Westport Rd. and becomes Old Sow Rd.. it ends where Old Sow Rd intersects with Center Rd. and it is doubtful that the highway was ever pushed further north. The terrain north of Center Rd. is extremely uneven and the road which has become Black Rock Turnpike follows a much easier course as it goes up the Aspetuck River valley and over Jump Hill. A road following the same route as modern Black Rock Turnpike was established very early; probably in the mid 18th century since many house of that period are found along its length and because it is mentioned adn mapped by the British during the Danbury Raid in 1777. With a convenient road like this passing up to and over Redding Ridge, there certainlt was no incentive to push Wilson's road further north nor to construct a northern section of this highway in Redding.

The last of the upright highways to be considered here is Burr St. Very little of the original highway is still in existence, at least in Easton and Redding. The road enters the western corner of Easton across Division St. and runs a very short distance before running into Black Rock Turnpike. At one time, the section of Black Rock Turnpike that runs north to the intersection with Wesport Rd. was Burr's Upright Highway. With the flooding of the Hemlock Reservoir, however, Black Rock Turnpike had to be moved westward where it took over the identity of Burr's St.. From Westport Rd., the highway jogged slightly to the west and then passed through one of the oldest sections of Easton, Gilbertown, to become Norton Rd.just north of the Gilbertown Cemetary. Norton Rd. today degenerates into an impassible dirt track north of Freeborn Rd., but much of its route northward over the top of the ridge that separates Easton and Weston, can still be substantially traced on foot. The highway eventually intersected with Den Rd. (never paved and now effectively closed to public traffic.). It then proceeded north to become Greenbush and Sanfordtown Rds. in Redding stopping only at the cross highway boundary road at the Redding green. The upright highway solved the problem of north-south travel, but getting east to west was another matter. The geography of Easton and Redding in characterized by a series of north-south running ridges. Thus when the north-south upright highways were being laid out, they extended along the ridges. This is one reason why they could be so straight. There were few elevated areas or large geographical obstructions along these ridges around which the highways would have to be rerouted. Going east to west, however, necessitated crossing these ridges and the intervening river valleys therefore causing the traveler to be almost constantly climbing precipitous hills or descending into steep sided valleys. Great Hill on Cross Highway in Redding is a good example. In traveling east to west on this road, once you have climbed the 150 feet of hill on modern Church Hill Rd., you pass over a short level stretch of road around the intersection with Newtown Turnpike. Then, as the name implies, you descend the 200 feet of Great Hill to the Little River valley floor only to start up the other side as soon as you have crossed the river. Similar climbs and descents are now waiting for you on Great Pasture Rd. and Diamond Hill before you finally reach the relatively level area of Seventy Acres Rd.

A solution to the problem of east-west travel in northern Fairfield (travel across the long lots)was partially provided by "cross highways." These highway obviously did nothing to reduce the elevations over which the traveler had to climb, but they did provide a cleared right of way which snaked back and forth, up and down the hill sides. The series of hairpin turns, such as the one that still survives on Church Hill Rd., served to reduce the grade up which your horse had to pull your wagon or up which you yourself had to walk. In the process of course, the length of the route that you had to travel was somewhat increased.

In 1734 the town of Fairfield voted to lay out and construct the cross highways. This probably coincided with the first movement of settlers onto the long lots. As with most road building projects on which the colonial towns embarked, the vote was not acted upon until 12 years later, a time in which the pace of settlement in the long lots had increased, thus increasing the pressure on the town to ease the burden of cross lot travel. The roads were probably not completed until 1758.

Depending on how they are counted there were six or seven of these cross highways built in whole or in part. The first and last respectively were the Long Lots Rd. to Fairfield Woods Rd. boundary road and the Cross Highway boundary road in Redding. Both of these were laid out in the 17th century and were not part of the planned program of cross highways mentioned above. The identity of the other cross highways constructed after 1746 are obscure. Old records frequently refer to the same roads using different highway numbers. Thus the 4th cross highway for one writer becomes the 5th cross highway for another. By ignoring numbers and looking for older roads that ran across most of the town, perpendicular to the upright highways, the major cross highways for Easton can be at least tentively identified. (Redding had only the northern boundary road which still retains the name Cross Highway.)

The most southerly of the cross highways apparently run just south of the present Easton border in Fairfield. In terms of todays roads, this highway consisted of Jefferson and Congress Streets running all the way from Burr St.. These roads are not a continuous line today but rather consist of disconnected segments because of the intervention of the Merritt Parkway, constructed in the late 1930's. The next or 2nd cross highway was almost certainly Beers Rd. which, before the Hemlock Reservoir was created in 1914, began at Burr St. and proceeded east to its present starting point at Wilson's Rd. (This section included what is today Division Rd. on the east side of the reservoir.) The road then proceeded, as Beers does still, to Sport Hill Rd. on the other side of which it follows the route of modern Flat Rock Rd. to Park Ave. Almost equally certain is the 3rd cross highway which appears today as Westport Rd to Center Rd. Then Center Rd. to Adams Rd. and along Adams Rd. to North Park Ave.

The 4th and 5th cross highways, however, are much less certain. We know that for Weston (the westem long lots.) seven cross highways were planned and were at least partially laid out (including the cross highway boundary road in Redding). This would argue strongly that the same number had been planned for the eastern long lots. Confusing the issue however are old documents and land records which tend to call Rock House Rd. Either the 4th or 5th cross highway. The reason for this inconsistency is not clear. Possibly two cross highways had been planned above the line of Westport and Center Rds. and even partially constructed but had not been used, had fallen into disrepair and thus forgotten. It is quite possible that the 4th cross highway was in fact Silver Hill Rd. The section that would have run to the west of Black Rock Turnpike to Norton Rd. was never completed and the steep hillside of Flirt Hill over which it would have to pass is probably the reason why. In addition, it apparently was never completed to the east of Sport Hill Rd. to Park Ave. This would leave the line of Valley Rd. to Staples Rd and Sunny Ridge as a probable uncompleted 5th cross highway. Rock House Rd. which until recently ran all the way to Black Rock Turnpike and continued west as the now disused Den Rd., would then be the 6th cross highway even though it is frequently refered to in contemporary documents as the 4th cross highway.

The confusion here is quite probably the result of the pattern of settlement in infant Easton. When the cross highways were being laid out between 1746 and 1758, what is now Easton was just beginning to be settled. As settlers moved into the area, they tended to concentrate in communities in the west, Gilbertown (the area around the Bluebird Inn and Easton swimming pool), and in the east, the Mill River Valley (under the Easton Reservoir). There was very little settlement in the northem portions of this area. Therefore, although the location of the 4th and 5th cross highways were determined, there was little need to construct them since there were so few people in that area to use the roads. Even if the rights of way had been cleared of trees and brush, disuse would have quickly allowed them to revert to forest. The sections that appear to remain were quite probably in the area of one or two outlying farms whose owner found segments of these cross highways useful as access roads to get cattle back and forth to pasture. Farm access roads frequently became town roads and were paved in the 20th century.

This of course leaves the question of why Rock House Rd as the 6th highway was constructed and maintained. The answer to this lies in Redding. Redding was settled beginning at least 30 years before Easton. Therefore, by the period when the cross highways were being built, Redding was a thriving community, having set herself up as an independent parish as early as 1729. Rock House Rd., running just south of the Redding border, would have been a convenience to those residents living in the southern part of the town. As a result the road would have been used and kept open.

A quick glance at the roads just outlined on a map will show that, unlike the upright highways, the cross highways were far from straight. Again the difficulties of travel from east to west across the town can be invoked as the explanation. This difficulty is also reflected in the early specifications for these roads in that they were originally supposed to be 20 rods (330 feet) wide. This extraordinarily wide right of way could have been seen as necessary to insure sufficient land to put in the hairpin turns or switchbacks that were necessary to lessen the grades of these roads up steep hills.

Another reason for the wide right of way might be to deal partially with the problem of erosion and mud. When wide roads were laid out in most early American communities, it was usually done to ease drainage problems. The center of the right of way in these roads always consisted of an 18 to 20 foot area that was bare dirt, kept free from vegetation by heavy traffic. During the wet season, however, spring rains turned these dirt tracks into a sea of mud making passage of horses and riders difficult and of carriages and wagons almost impossible. At such times it was possible to travel up the sides of the right of way where there had been little traffic during the early parts of the year and thus were not stripped of vegetation which held the soil and maintained relatively firm footing.

Where roads ran up or down steep grades the mud season posed a special problem. Water would run down these steep grades and the steeper the grade, the faster the water flow and the greater the erosion of the roadbed. In many early hill roads deep gullies were formed after even a few years of existence. In some remaining remnants of the early steep roads, which have not been recently graded or paved, entrenching has lowered the roadbed eight to ten feet below the old ground surface level. Building hairpin turns on these roads reduced the grade and consequently the rate of water run off, but it did not completely stop erosion. Vegetation along the sides of the right of way would have further slowed water run off and retarded erosion. Regardless these measures were only partially successful as existing relies of these old roads demonstrate. With respect to the cross highways, the original intentions of the road planners may have been to deal with these problems by employing the extraordinarily wide right of way, but expediency, or maybe it was just the cost of acquiring the extra land, prevailed and t 2 years after the first proposal, the road width was reduced to the standard six rods (99 feet).

As should be apparent from the above discussion, traveling the colonial and early American road system was not easy, nor was it fast. In addition to the problems of the mud season, there were numerous others. Although the right of way of any of these roads were supposed to be cleared of obstructions, they rarely were. If a rock was too large to be removed easily from the traffic path by an ox team, it was left and traffic was expected to maneuver around it, or, if the rock was low enough, to go over it endangering wheels and axles. Trees were cut down but stumps were rarely removed. They were left to rot and again traffic had to maneuver around them. If the traffic on any given stretch of road was insufficient to keep the vegetation down, brush and small trees quickly invaded the right of way. Farmers living off of these roads were expected to keep them clear of obstructions, but the town records are filled with votes to deal with highways that had become impassible and which need to be maintained.

In addition to hills that had to be climbed and streams that had to be forded, swamps also had to be crossed. If the swamp was small nothing was done and traffic was expected to wade through it. Occasionally there was an attempt to firm up the roadbed by pitching rocks into the slime along the right of way or by setting sections of logs side by side across the soft areas, but with the weight of passing traffic, the rocks frequently sank too deep to be useful and logs quickly rotted and broke through. If the swamp was large, an attempt was made to build an elevated section or causeway across it by using rocks and dirt to build up the right of way. This is in part the origin of the term highway. A relic of this technique can still be seen in the small segment of old Stepney Rd.(Rt#59) in Easton which passed immediately to the east of the Baptist church. The elevated roadway extends for several yards out into the swamp. It apparently was insufficient and the town voted to simply go around the edge of the swamp, an alternative frequently employed by other early American road builders when faced with a swamp.

Not only natural factors but humans also impeded movement along early roadways. Farmers frequently looked upon the roads that passed through or adjacent to their farms as being extensions of their lands. Thus the grass growing along the sides and into the right of way was a resource to be utilized by his cattle. Negotiating one's way through a herd of grazing cows is a common annoyance mentioned by early travelers. Farmers even went so far as to erect gates across the roadway so that their cattle did not wander too far away. Town meetings down to the late 19th century were constantly issuing instructions to their highway surveyor and haywards to remove such obstacles.

Is it any wonder, with all of these inconveniences, why people who traveled during these early periods, preferred traveling by water and if water transportation was not possible, they preferred to stay home. The state of the roads was one reason why inland communities tended to be close. To run from Easton or Redding into Bridgeport or Danbury was not a 20 minute trip as it is with paved roads and high performance automobiles, but rather a several hour to half a day expedition, depending on from where you started. Thus trips to town were infrequent and done only for pressing business or to pick up such goods as could not be produced in the community or on the farm. Needs for social contact and entertainment were satisfied within the neighborhood and this created a closeness which has become one of the notable characteristics of colonial and early American life.

As imperfect as the roads were and as difficult as travel over them was, the grid of upright and cross highways was an important one. At its most basic, this road structure allowed access to the interior lands that would become Easton and Redding and thereby encouraged settlement, in the same way that paved roads and automobiles today have turned these towns into suburbs. In addition, they allowed movement between neighborhoods within these areas as well as movement between outlying farms and the meeting house, general store, and tavern that were so important to the isolated farmer. In a very real sense they made these outlying farms possible and road crossings often determined where whole neighborhoods would develop.

In a broader sense this early road structure determined the present pattern of roads in these towns as well as their traffic flows and patterns of modem residential development. As Easton and Redding moved into the 20th century, the old upright and cross highways were the first to become paved and thus they became the major arteries into and out of town, as well as between areas within the towns. These early paved roads constitute the basic road structure of this area. This basic structure would be modified as old farm access roads became paved to give access to more remote areas of town. More recently it would be modified by new subdivision roads which follow a map line set up to most efficiently develop a parcel of land. But the basic structure still remains and therefore to understand the interactions within the towns of Easton and Redding as well as their development, it is necessary to understand the patterns and nature of the highways that were first built in these areas and called upright and cross highway.

"Turnpikes of Easton and Redding" by Daniel Cruson

As the 18th century drew to a close, the first stirring of the Industrial Revolution were being felt both in Europe and the United States. One of the prerequisites for this industrial development was a transportation system which provided for easy and inexpensive movement of raw material to mills and factories and the movement of finished products out to markets at home and abroad. In coastal areas, where there was ready access to water, adequate transportation was much less of a problem than it was in interior areas like Easton and Redding where there was neither direct access to the ocean nor any navigable rivers down which products could be floated by barge or river boat. The interior, therefore, was forced to rely on overland transportation and, until the development of railroads about the middle of the 19th century, this meant reliance on wagons and the roads over which they had to pass. The state of the roads in this area, however, was very poor. Overland transportation even for a single horse and rider, was difficult and, at times such as the wet spring season, nearly impossible as dirt roadways dissolved into a sea of mud. This was true not only in central Fairfield County but in the entire nation as well.

A major problem that faced the United States in the 1790's, then, was how to improve the state of the Nations roads. Road construction and repair was a very expensive process, and the federal government had little in the way of money, especially since direct taxation, such as the Income Tax, would not appear until the 20th century. In addition there was a strong feeling among most citizens that the federal Government should stay out of the road building business. The answer to this dilemma was to turn the business of road construction and repair over to private individuals and the most efficient means of doing this was through incorporation. Thus began an economic period referred to by historians as the Turnpike Movement.

Individual states, such as Connecticut, had the right to charter and thus create corporations. A corporation is a legal entity which is entitled to sell shares of ownership in itself, called stocks, in order to raise the money necessary to set itself up in business. Corporations had occasionally been chartered for purposes of colonization and various manufacturing processes in the early colonial period. With the formation of state governments in the wake of the Revolution, however, the number of incorporations increased until, by the decade of the 1790's, this growth became dramatic, especially as corporations were applied to transportation and the construction, repair, and improvement of roads and bridges. One type of corporation that was specifically set up to construct or repair a road then was the turnpike company.

To form a turnpike in Connecticut, as in most other states, it was first necessary for a group of men to draw up a petition to be submitted to the state legislature asking for the privilege of incorporation and proposing a route along which the road would be constructed or, in the case of an already existing road, improved. Once incorporation was granted, the founders of the turnpike corporation would meet, elect officers, and determine how much money was going to be needed to construct and maintain or improve the roadway. Once this was determined, the corporation would issue and sell stock. By doing this the corporation sells small pieces of itself. The money that is raised by this process is then put toward the acquisition of land along the proposed route, if a road was not already in existence, and toward the actual construction or improvement of the roadbed.

It is important to remember that the turnpike company was a business venture and that the purchasers of these early company's stock expected to receive dividends, a share of the company's profits, in return for their stock purchase. But where was the money to come from that would constitute the company's profit? In the corporation charter, the turnpike company was given the right to charge a fee or toll to all of those who would be using the road. The toll rate was carefully controlled by the state legislature and was to be collected at a tollgate placed at a convenient location or locations along the length of the road. The tollgate usually consisted of a small house in which the toll taker could take refuge in inclement weather, and a long pole or pike that could be rotated horizontally on a post to block the road until the toll was paid, and then rotated out of the way to allow the passage of the toll paid traffic. It is the turnpikes which gave these roads their names.

The tolls which supplied profits and thus dividends, usually made the formation of turnpike companies a very attractive venture in areas where there was a substantial volume of traffic passing in and out of a region. This accounts for the large number of turnpike companies that were formed in the 1790's and through the first three decades of the 19th century. By 1800 there were 219 turnpikes and bridge companies in the U.S. but only six manufacturing concerns were organized as corporations. This ratio of manufacturing to transportation corporations would be reversed by the second quarter of the 19th century but the figures for the early years of this century clearly show how profitable and popular the turnpike movement was. Entrusting road building to private hands rather than to the government was clearly successful, at least in the early stages of the Industrial Revolution.

What was true for the nation, was no less true for the state and for the towns of Easton and Redding. The basic structure of roads in these towns had been created by the system of upright and cross highways constructed in the late 17th and early 18th centuries, but these highways had been laid out first on paper without regard for the actual patterns of traffic created by local geography nor the traffic patterns that developed as the communities grew and prospered. Modifications and improvement of this basic road structure, then, would be accomplished by turnpike companies as they perceived the need for new traffic patterns or improvements to old ones, and acted on these needs for their own profit.

A good example of one of these local transportation companies is the Stratfield and Weston Turnpike Company. [note: Weston until 1845 included Easton] Chartered as the result of a petition to the General Assembly in 1797, this company was permitted to issue stock and with the proceeds from this stock sale they were to repair and modernize a stretch of road that began "at the foot of the hill...before the Baptist meeting house, and extend north in Jackson's Upright Highway so called until it comes to the Cross Highway about 25 rods [about 400 feet] above the dwelling house of David Silliman" in Easton. This road today is the section of Sport Hill Road that runs from the Baptist church, which still stands on the hill in Stratfield just below Fairfield Woods Road, north to Rock House Road in Easton. Apparently this stretch of road was in almost impassible condition and the formation of the Stratfield and Weston Turnpike Co. was a means whereby the road could be made fully usable without having those repair become the concern of the towns involved and without having to raise taxes to pay for it.

Also by the provision of their charter, this company was entitled to set up a toll house and turnpike and to collect tolls according to a fee schedule that was established by the General Assembly. The toll house and turnpike were set up at the base of what is today Sport Hill Road, across from Jefferson Street, where entrance to the General Electric corporate headquarters driveway is situated. There it remained for 89 years until the company's charter was repealed and the road made free in 1886.

The fees collected at this tollgate were very carefully regulated since turnpikes were seen as a type of natural monopoly over which the traveler and resident had no control. For the Stratfield and Weston Turnpike a fee of 6.2 cents could be collected for every loaded wagon (half that fee a the wagon was empty), 4 cents for a loaded one horse sleigh, 12.5 cents for a pleasure carriage of any kind, 4 cents for a man on horseback, and 1 cent for every sheep or pig that was herded through the tollgate. A penny of course was worth more during this period than it is today. According to government statistics for consumer prices at various time in our history, one penny was about 7.5 times more valuable in 1800 than now. Therefore in today's money every sheep or pig would cost 7.5 cents, every man on horseback would be charged 30 cents and any pleasure carriage would have to pay almost a dollar for the privilege of driving up Sport Hill Road into Easton along a fully modern gravel road.

Although these toll rates might seem burdensome, especially for anyone who used the road regularly to pass back and forth between Easton and Fairfield or Bridgeport, there were exceptional circumstances under which the tolls did not have to be paid. These were also carefully spelled out by the General Assembly. Exempt were all persons going to or returning from a funeral, public worship, or a saw or grist mill. In addition, " all officers or soldiers on days of military exercise on command who must necessarily pass through...the gate," were exempt, as were all residents who "live near the place where the toll gate is erected, whose necessary daily calling requires their passing the gate.”

The General Assembly also regulated the way in which revenues from tolls would be disbursed. As with any business, a portion of these revenues would be used to cover the cost of repairs and maintenance of the roadbed and payment of a toll taker. In a modern corporation, profits, their revenues after all costs are deducted, are then distributed to the stock holders as dividends in proportion to the number of shares of stock owned. The Stratfield and Weston Turnpike Co., however, was only allowed to distribute an amount of profit to each stockholder equal to 12% per year of the total amount that the stockholder had paid for his stock. All money that was left after these dividend payments had been made were to be used to pay back the money that the company had collected from its stockholders as a result of the original stock sales. In this, the money from stock sales was being treated as a loan rather than a true investment in the company. Ideally the amount of money that the stockholder had made available to the corporation, would be slowly returned to the stockholder until he was entirely paid back. Then there would no longer be a need to collect tolls and the road would become free. Since we know that the Stratfield and Weston Turnpike Co. continued to collect tolls until 1886 when Fairfield County made all of its turnpikes free, it is fair to assume that the company never had large enough revenues to pay back its stockholders, although the enterprise must have been fairly profitable or it would not have survived as a corporation for almost 90 years.

Older than the Stratfield and Weston turnpike Co. by about six months was the Fairfield, Weston, and Reading Turnpike Co. which received its charter in May of 1797. This company improved and maintained a section of road that ran from the home of Samuel Wakeman Jr. in Easton, across Redding Ridge to the meeting house in Bethel, which was then part of Danbury. The Samuel Wakeman house is still in existence and it sits on route #58, opposite the mouth of Freeborn Road. The turnpike extended from that point north along route #58 to Sunset Hill Road. It then went north along Sunset Hill and over Hoyt's Hill into Bethel as far as the Congregational church. (The section of modern route #58 which runs from Sunset Hill Road to Putnam Park, is a new stretch of road that was constructed around the turn of this century to facilitate access to the park.)

The tollgate for this turnpike was located " at the house of Samuel Thorp," which was apparently located just north of Jump Hill, on the flat stretch of road which lies just south of the Redding border. Having their tollgate so far south on the road posed a revenue problem, however, since many people were using just the northern sections of this road and thus not paying tolls for the use of the road. This problem materialized very early in the company's history, for in 1798, a little over a year after their formation, they petitioned the legislature and were granted permission to establish a tollgate on the northern portion of the road provided that someone traveling the full length of the road would only have to pay at one tollgate and not at both. Unfortunately the location of this upper tollgate was never mentioned in the legislative records and is therefore unknown. It continued to function, however, the road was declared free in 1834. The entire road became free when the company's charter was repealed in 1838.

Another turnpike was created in 1832 whose history was to become closely tied to the Fairfield, Weston, and Redding Co.; The Black Rock and Weston Turnpike. The company that was chartered to construct and improve this road was permitted to operate from Black Rock Harbor northwesterly to a point just north of today's Westport Road (route #136). The purpose for constructing this road was obviously to facilitate the movement of farm produce and other small locally produced goods to the harbor for transshipment by water to markets in places like New York City and the South. The road became an even more valuable link to the coast when it was connected to the Fairfield, Weston,and Redding Turnpike by a short stretch of road running from Westport Road to Freeborn Road creating what is still known as Black Rock Turnpike running from Bethel to Long Island Sound. The road was made entirely free when the Black Rock and Weston Turnpike Co. was dissolved in 1851.

Among the other roads in this area which began as turnpikes are Newtown Turnpike and Hopewell Woods Road in Redding. These roads are what remains of the Newtown and Norwalk Turnpike which was chartered in 1829 to run from the " foot of Main Street in Newtown, passing near the Episcopal church in Redding, through the westerly part of Weston, (and) ultimately to the great bridge in Norwalk at the head of Norwalk Harbor." Again the motive for building this road was to facilitate the movement of goods from the interior to the coast. By 1841, the northern portion of this road running through Redding and Newtown was made free and tolls were dropped on the rest of the road by 1851.

The Fairfield County Turnpike, which ran through both Easton and Redding, had a relatively short life and ran along a very confusing route. It was chartered in May of 1834 and its charter was repealed in 1848 after two changes in location had been approved in 1836 and 1837. The final route of this turnpike was supposed to have run from the northern end of the Black Rock and Weston Turnpike (where routes 58 and 136 intersect today) across Easton, through eastern Redding to the southwesterly portion of Newtown, and passing ultimately into Brookfield ending at "Meeker's Mill." In terms of modern roads, this turnpike appears to have passed up Westport Road (route#136) to Staples Road, up Staples to Valley Road, and then followed Valley Road through Poverty Hollow in Redding and Newtown, turning down Flat Swamp Road and passing through Dodgingtown.

A longer lived turnpike, but one with an equally unclear route was the Weston Turnpike. It was chartered in May of 1828 and only became a free road when Fairfield County cleared itself of all turnpikes on March 24, 1886. The route is described as running "from Philo Lyons to the Black Rock Road in Fairfield with a branch from Fairfield to the Academy in Weston." The location of Philo Lyons house is not known precisely but it probably stood on Morehouse Highway about one mile north of the junction with Beers Road. From this point on Morehouse Highway, the turnpike probably ran south to Beers Road, then west along Beers beyond Wilson Road and under what is now the Hemlock Reservoir, to end at Black Rock Turnpike. The section of this turnpike which ran to the west of Wilson Road was closed and abandoned when the Bridgeport Hydraulic Company built the reservoir in 1914. The "branch from Fairfield to the Academy in Weston," was probably Wilson Road from Beers to Westport Road, to the Staples Academy building which still exists as part of the parish hall for the Congregational Church.

A turnpike about which we have very little information is the Simpaug Turnpike in northwestern Redding. We do know that a company was chartered to build this road in 1832. We do not know when the road was made free but it must have happened by 1886 when the County abolished its turnpikes. Modern road names suggest that the turnpike started in the business section of Bethel and ran southwesterly along what is now route#53 and Side Cut Road to the village of West Redding. From that point it appears to run along the railroad tracks south and west to the Topstone area where today it swings out and joins the Ethan Allen Highway (route #7). It is not known if the turnpike ever ran beyond its intersection with route#7. It is also not certain where the name comes from unless it refers to the Simpaug ponds which lie near its point of origin in Bethel.

The road that started as the Branch Turnpike is still an important east-west corridor through Easton. The company that built this road was incorporated in May of 1831 and the road itself extended from Bennett's Bridge across the Housatonic River (just north of the Rochambeau Bridge which carries route#84 traffic across the same river today.), through south and east Newtown, Monroe, Easton, and Fairfield, ending in Westport. Today in Easton this road is Stepney Road (route #59) running from the village of Upper Stepney to the Easton Rotary (The four way stop below Union Cemetary and the Baptist Church.) From the Rotary it becomes Westport Road (route #136) and runs southwesterly to a point just south of the village of Westport. This road became free when its charter was repealed in 1851, 20 years after it had been founded.

One further turnpike must be considered for the sake of completeness of this treatment if not for the importance of the road itself; the Sherman and Redding Turnpike. The company which built this road was chartered in 1834 and the road ran from the town of Sherman to either the Newtown and Norwalk Turnpike in Redding or to the Northfield Turnpike in Weston. According to Frederick Woods, who wrote the definitive book on the turnpikes of New England, "it is clear that the plans were carried out, but it is impossible today to pick out the location." According to a petition which was filed with the General Assembly in 1846, the turnpike was "never demanded by public necessity or convenience and that for six years it had been wholly and entirely abandoned, and consequently impassible and useless." From this it would appear that the turnpike had a life span of less than six years. All that remains of the road today is a short stretch of road in central Redding which is still called Sherman Turnpike, running from the Redding Green south to Newtown Turnpike. Other sections of this turnpike may still be in existence under other names but since its route north of the Redding Green is unknown it is impossible to be sure that any of these other roads lie along the old Sherman Turnpike.

The Sherman Turnpike was an apparent financial failure which underscores an important aspect of the entire Turnpike Movement; turnpikes were a business, supported by private financiers and dedicated to improving overland transportation without resorting to federal government control and expenditures nor requiring tax revenues. As with any businesses, some were failures like the Sherman Turnpike and others were highly successful such as the Branch Turnpike which became Westport Road and the Stratfield and Weston Turnpike which became Sport Hill Road. The failures had little impact on this area beyond supplying an occasional place name or reference in an old land deed. The successes, however, because they served a necessary function such as getting goods and people from the interior to the coast, or supplied a public convenience such as getting people across town easily, survived and became improvements and modifications of the basic road structure in this area. The Turnpike Movement was the most important phase in the development of local roads and transportation between the establishment of the basic road structure with the upright and cross Highways of the late 17th century and the concerted push during the early 20th century by the towns themselves to pave all of their roads. The turnpikes also stand as one of the highest expressions of the American ideal that the most desirable way to accomplish something is not through government effort and expenditure but rather through the exercise of Capitalism and private enterprise.

Redding and Easton
by Daniel Cruson
*Great Photos of Early Redding

The Old Turnpike thru Georgetown- by Wilbur F. Thompson. For many years after the first settlement of our state, the roadways connecting the towns were very poor. Many were mere "bridle paths," others were Indian Trails widened into "Cart Paths." One of these was the Indian Trail leading up from the Sound, at what is now known as Calf Pasture Beach, through the section now known as Georgetown, into what is now the city of Danbury. It was over this trail that the eight families left Norwalk in 1684, to found the new town of Danbury. And for many years this trail, widened into a cart path, was the only connecting link between the two places.

As the town of Danbury grew, the need of a better means of transportation became apparent. A survey was made and a new highway was opened up. From Danbury the turnpike followed South Street to what is now Reservoir Road, to Long Ridge Road, into West Redding, up over the Umpawaug Hill, Redding, through what is now Boston district and Georgetown, and on to Norwalk. The right of way was six rods wide. It was known as the "great road" from Danbury to Norwalk.

[On South Street, Danbury, there is still a mile-stone bearing the date of 1787, "68 miles to New York, 67 miles to Hartford."]

In 1723 Nathan Gold (Gould) and Peter Burr of the town of Fairfield sold to Samuel Couch and Thomas Nash, of the same town, one hundred acres of land in the Parish of Redding, town of Fairfield, "said land lyeing on both sides of the great road, that leads from Norwalke to Danbury," showing that the road was in use at that date.

In 1792 the town of Redding voted to reduce the width of the Danbury and Norwalk road, in Redding, to four rods.

In 1795 the "Norwalk and Danbury Turnpike Company" was formed. The company was incorporated for the purpose of "making and keeping in repair the great road from Danbury to Norwalk - from Simpaug Brook, Bethel, to Belden's Bridge, Norwalk (now Wilton) and to erect gates and collect tolls for the maintenance of the same." Toll gates were erected at intervals along the road. One was north of where Connery Brother's store once stood in Georgetown (likely about where Georgetown Auto Body is located). This was the only road of consequence in the area and soon became the Post Road.

Proof of its importance is indicated by the location selected as Redding's first Post Office. On December 22, 1810, Redding's first Post Office was established with Billy Comstock as Postmaster, keeping office in his house which was located at what is today the corner of Umpawaug and Route 107. Across the street was a tavern which was also the place where horses were changed and fresh horses put on. The tavern serviced the stage coaches as they passed through Redding to meet the Danbury and Norwalk stage. This location was known as Boston Corners, and for some time Darling's Corners as well. Later the horses were changed in Georgetown at Godfrey's store on Old Mill Road.

Clark's Map of 1856 showing Old Mill Road on the right. You'll notice Old Mill
Road was far more popular than Route 7 (road on the left) at that time period.

As the towns grew and the intervening section became thickly settled, the "Old Turnpike" became a congested thorough-fare. Historian Wilbur F. Thompson explained that his grandfather, Aaron Bennett, said "in his boyhood days (1818) there was an unending procession of great canvas-topped freight wagons, stage coaches, slow-moving ox carts. Travelers on horseback and on "Shanks Mares" (pedestrians) passing both ways night and day." At about this date the Sugar Hollow Turnpike was opened up. Starting at Belden's Bridge, Norwalk (now Wilton) on the west side of the Norwalk River, up through Georgetown and into the Sugar Hollow Valley, along the course of the river, through the town of Ridgefield, and into the western side of Danbury. This is now [Route 7] the state road from Danbury to Norwalk.

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