5.0
(5)
16
riders
5
rides
Touring cycling around Gaylordsville, Connecticut, offers access to extensive scenic trail networks within the picturesque Housatonic River Valley. The region features a mix of terrain, including relatively flat sections along river trails and routes with moderate elevation gains. Cyclists can explore multi-use greenways, low-traffic riverside roads, and paths that traverse both paved and packed dirt surfaces. The landscape is characterized by the Housatonic River, providing scenic views and contributing to the valley's charm.
Last updated: May 31, 2026
5
riders
31.2km
02:10
550m
550m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
30.1km
02:06
420m
420m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3
riders
33.4km
02:08
410m
410m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
3
riders
44.1km
02:43
420m
420m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(4)
4
riders
49.8km
03:15
450m
450m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.
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With its spring in Massachusetts the Housatonic River flows for 149 miles to southern Connecticut into Long Island Sound. The Appalachian Trail follows the river from the covered wooden Bulls Bridge to Falls Village. The river is also a popular whitewater paddling destination with mostly Class I to Class III rapids.
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This is one of three old covered wooden bridges spanning over the Housatonic River. While the one at Cornwall is still intact, the original Old Covered Bridge in Sheffield was destroyed by fire and had to be rebuilt.
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This is part and beyond is part of the Appalachian trail and is recreational part that is open to bicycles. It is a dead end tho!
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There are 6 touring cycling routes around Gaylordsville, offering a variety of experiences for different skill levels. You'll find a mix of moderate and difficult routes to explore the scenic Housatonic River Valley.
The touring cycling routes in Gaylordsville offer diverse terrain. You can expect a mix of paved and packed dirt surfaces, with sections ranging from relatively flat multi-use greenways, like parts of the New Milford River Trail, to routes with moderate elevation gains. Many routes follow low-traffic riverside roads, providing varied touring experiences.
While there are no routes specifically classified as 'easy' in our guide, the region does offer sections suitable for families and less experienced cyclists, particularly along the New Milford River Trail. This multi-use greenway features relatively flat terrain, making it a good option for a more relaxed ride. For a moderate challenge, consider the Bulls Bridge loop from Sherman.
The area is rich in natural beauty and historical landmarks. You can cycle past the picturesque Lake Waramaug State Park, visit the historic Bulls Bridge, or enjoy scenic views from the River Trail. The Housatonic River itself is a central feature, providing stunning views along many routes.
Yes, many routes in Gaylordsville are situated within the Housatonic River Valley and offer beautiful riverside views. The Housatonic River – Skiff Mountain loop from Kent is a great option that specifically highlights the river. Additionally, the Bulls Bridge – River Trail loop from Erickson Corner leads through the Housatonic River Valley, providing ample opportunities to enjoy the river's charm.
For those seeking a challenge, Gaylordsville offers several difficult routes. The Lake Waramaug – Baldwin Hill loop from Kahn Preserve is a demanding 19.8-mile trail featuring significant climbs and scenic lake views. Another difficult option is the Leonard Pond – Hatch Pond loop from Sherman, which is the longest route in our guide at nearly 37 miles.
Yes, many of the touring cycling routes around Gaylordsville are designed as loops, allowing you to start and end at the same point. Examples include the Lake Waramaug – Baldwin Hill loop from Kahn Preserve, the Housatonic River – Skiff Mountain loop from Kent, and the Bulls Bridge – River Trail loop from Erickson Corner.
The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the varied terrain, the beautiful Housatonic River Valley scenery, and the well-integrated trail networks that offer a mix of challenges and picturesque views.
Yes, Gaylordsville is strategically located within several significant cycling networks. It serves as the northern terminus for a section of the New Milford River Trail, which overlaps with the Western New England Greenway (U.S. Bicycle Route 7). The area is also part of the broader "HouBike" Trail, or Housatonic Covered Bridge Bicycle Trail, a 45-mile network connecting Litchfield County communities along the Housatonic River. You can find more information about the HouBike Trail on the Housatonic Heritage website.
The spring, summer, and fall months generally offer the best conditions for touring cycling in Gaylordsville. Spring brings blooming foliage, summer provides warm weather, and autumn showcases vibrant fall colors, making for particularly scenic rides. Always check local weather conditions before heading out.
While Gaylordsville itself is a small community, the surrounding towns and villages along the Housatonic River Valley offer various amenities. It's advisable to plan your route to pass through larger towns like New Milford or Kent for cafes, general stores, and other services. Always carry sufficient water and snacks, especially on longer rides.
Parking availability varies by trailhead. For routes utilizing the New Milford River Trail, you can often find parking at designated access points or nearby parks. For other routes, starting points near town centers or public access areas typically offer parking. It's recommended to check the specific route details on komoot for parking suggestions related to your chosen tour.


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