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Biking Trails & Road Bike Loops in Redding, Connecticut (CT)  
   

Road Bike Loops

Short Hill Intensive Loop (Shown via Google Maps)

Start at Mark Twain Library, Make Right follow Route 53 to Stop Sign, Left Up Hill Road, Make a Left Just Before Redding Nursery, Follow to Old Stage Coach Rd., Make Right and Follow to Gallows Hill Rd., Make Left and Follow to Route 53, Make Left and then Quick Right onto Umpawaug Rd., up Umpawaug Hill, down Umpawaug Hill, Left at Diamond Hill Rd., about a quarter mile on right turn on Fox Run Rd., at the top of Fox Run stay left onto Umpawaug Rd. and then quick right onto Seventy Acres Rd., up Seventy Acres hill and take Windy Hill Rd. on the right, follow to Old Redding Road and make a right, make a right onto Umpawaug Rd., down to Diamond Hill again and make left, follow Diamond Hill Rd. to Route 53, make a right and Mark Twain Library is on your right.

Looooooong Hill Intensive Loop:

Start at Mark Twain Library, Make Right follow Route 53 to Stop Sign, Left Up Hill Road, passing the Redding Nursery, look for Cross Highway branching to the Right, follow Cross Highway to Route 58 (Black Rock Trpk) and Make a Left, about 1/4 to a 1/2 mile down Rt. 58 stay Straight where the road curves and Head up Sunset Hill Rd., Follow Sunset Hill down to the Wolfpit Area and Make a Left to connect with Rt. 58 again, Make a Right toward Bethel, 1/2 mile on your left will be Hoyts Hill, Take Hoyts Hill and follow through to Milwaukee Ave. Bethel, at Stoplight take a Left and stay left up Chestnut Ridge Rd. follow into Redding, past the Redding Country Club, Make Right onto Gallows Hill Rd., Follow to Route 53, Make Left and then Quick Right onto Umpawaug Rd., up Umpawaug Hill, down Umpawaug Hill, Left at Diamond Hill Rd., about a quarter mile on right turn on Fox Run Rd., at the top of Fox Run stay left onto Umpawaug Rd. and then quick right onto Seventy Acres Rd., up Seventy Acres hill and take Windy Hill Rd. on the right, follow to Old Redding Road and make a right, make a right onto Umpawaug Rd., down to Diamond Hill again and make left, follow Diamond Hill Rd. to Route 53, make a right and Mark Twain Library is on your right...head to Redding Roadhouse and eat all you want.

The Ridge Loop:

Park at the Redding Boys and Girls Club (if crowded park at the Episcopal Church) head South on Route 58, after passing the Joel Barlow High School entrance start looking to take a left onto Pine Tree Road. Pine Tree is tight so be alert, Pine Tree Rd. will eventually turn into Rock House Rd. when you hit a 4-way stop sign make a left onto Sport Hill Rd. Follow Sport Hill to the end and make a left onto Stepney Rd. and then a right onto Poverty Hollow Rd. Make a left on Church Hill Rd. and get ready to climb! You'll come out on Rt. 58, just head across the road to your car.

To extend the above loop pass the Church Hill Rd. left and continue to Hopewell Woods, Rd. Make a left on Hopewell and continue until you hit Rt. 58, make a left and in 3/4 mile you'll make a right at the 4-way stop sign.

The Lonetown Loop:

Park at John Read Middle School, head South, at 4-way stop make a left onto Great Pasture Rd., follow and stay right until you hit Hill Rd. (Rt 107), once on Hill Road stay left and you'll soon be passing the Police Station and Town Hall. Follow Lonetown Rd. (Rt. 107) past Redding Country Club and after stop sign start looking to make a left on Limekiln Rd. Follow Limekiln Rd to end and make a left on Rt. 53. Follow Rt. 53 back to John Read Middle School.

More loops to come soon, feel free to add your own by emailing me map links or routes: bcolley@colleyweb.com.

Mountain Biking Trails

Huntington State Park
Acreage: 900
Miles of Trail: 7.5
Entrance: Sunset Hill Road

Easiest way to get there: Route 58 East or West. Coming from Bethel, you will pass Putnam Park Pond on your left, bear left at the fork following Rt. 58 for approximately 1.5 miles, Sunset Hill is to the left at the apex of a right-hand curve, you will travel up a steep incline for about 3/4 miles, Huntington State Park is on the right. Coming from Easton, your point of reference is the four way stop at the junction of Route 58, Cross Highway, and Church Hill, from there Sunset Hill is the third road on your right about 3/4 miles up. Also, see Tom's Notes below.

What is it like? Wide open. Very good place to introduce the children to the great outdoors. The trails are well maintained, there are four ponds and a lake(state permit required to fish), it is also open to horses and bikes

Tom's Notes: The map in the book provides a useful overview of the park. However, it does not include many key details, including the parking area on Dodgingtown Road, the full trail loop in Bethel, and the color codes for the trail. By far the best map of Huntington State Park is published by the Connecticut Department of Environmental Protection. This full color map includes point-to-point distances along the trail. You can download the map at http://dep.state.ct.us/stateparks/parks/huntington.htm.

The Sunset Hill Road parking lot is better known and more commonly used, but the Dodgingtown Road lot has some advantages. When you finish your hike and you return to that lot, you do not need to slog up the steep hill, which is often windswept. This other lot also has more parking. Alas, you do give up the views of the wolf and bear statues. To reach the Dodgingtown Road parking area, continue north past the Sunset Hill Road parking area.

Changes from Book III to Book IV: There are two updates to the map printed in Book 4: The open area north of the Sunset Hill Road parking area is now the Couch Hill Preserve, owned by the town of Redding. A description of this property may be found on page 22 in Book IV. Wood Road is labeled on the map in Book IV, but not in Book III. .

Topstone Park
Acreage
: 274
Miles of Trail: 3.69
Entrances: Topstone Road

Easiest way to get there: From Route 53, turn onto Umpawaug Road and follow past the Fire House and Red Schoolhouse, continue up Umpawaug, Topstone is the second road on the right, park at Topstone Town Park about a mile down the road on the left.

Tom's Notes: According to the Redding Park and Recreation Department, parking at Topstone is no longer limited to Redding residents. I would confirm this at the park during the summer season to make sure you do not get a ticket. Park near the entrance in the off-season where there are nine parking spaces. The gate is open during swimming season. (Users must purchase a pass to swim). There is no realistic parking on Old Redding Road or Topstone Road. The trailhead off Old Redding Road is by 74 Old Redding Road. There is adequate parking available on Topledge Road or White Birch Road. The trailhead off Topledge Road is between 23 and 26 Topledge Road. The trailhead to the Saddleback Trail off Old Redding Road is located near 140 Old Redding Road.

Changes from Book III to Book IV: The connection to Windy Hill is indicated in Book IV with the beginnings of a trail.

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History of Redding is a not a business or an organization..It's one person working to promote the history of his hometown
and surrounding areas. All costs are out-of-pocket so donations and/or sponsorships will allow me to dedicate more time
and effort to research and updates.