The best gravel rides around Gaylordsville
27
riders
5
rides
Gravel biking around Gaylordsville, located in Litchfield County, Connecticut, features a landscape shaped by the Housatonic River and its tributaries. The area's topography includes hills like "the Pinnacle" and Straits Mountain, providing varied terrain for cycling. Routes often utilize well-maintained dirt roads, offering access to natural features and scenic views. The region's natural features, such as Bulls Bridge and Lake Waramaug State Park, are accessible via these gravel routes.
Best gravel bike trails around Gaylordsville
- The most popular gravel bike…
Last updated: May 31, 2026
12
riders
54.5km
03:13
710m
710m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
13
riders
98.5km
05:31
1,110m
1,110m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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5
riders
63.5km
03:52
820m
820m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
30.7km
01:47
420m
420m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
42.3km
02:26
530m
530m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Tips from the Community
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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This is a tiny but highly scenic little park. The roads that circumnavigate Lake Warmaug are partially shaded and go right up to the water's edge, and the views out across the water are especially beautiful in the autumn. There is also camping, hiking, and kayaking here, as well as a couple small beaches for swimming.
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This small lake-side park comes equipped with picnic benches and plenty of trees to provide shade on a summers day. A great spot to take a break.
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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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Explore the Rock Tunnel, a 235-foot passage from the Shepaug Valley Railroad (1872-1948). It's a blast to go under during your hike, giving you a taste of the area's cool railroad history.
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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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fast moving is possible if you're running out of time ..or daylight. Like I did.
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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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Frequently Asked Questions
How many gravel bike trails are available around Gaylordsville?
There are 7 gravel bike trails documented on komoot for the Gaylordsville area, offering a variety of routes to explore the region's landscapes.
What kind of terrain can I expect on gravel bike trails in Gaylordsville?
Gravel biking around Gaylordsville features a mix of river valleys, well-maintained dirt roads, and forested areas. The topography includes hills like 'the Pinnacle' and Straits Mountain, providing varied terrain and elevation changes.
Are there any family-friendly gravel routes in Gaylordsville?
While many routes in the area are rated as difficult, the region's well-maintained dirt roads, such as sections of the River Trail, can be suitable for families looking for less technical rides. Always check the route details for specific difficulty and elevation before heading out.
What are some scenic spots or landmarks I can see along the gravel trails?
Many routes offer views of the Housatonic River. You can also encounter landmarks like the historic Bulls Bridge, or pass by Lake Waramaug State Park. The River Trail itself is known for its scenic beauty, especially in autumn.
Are there any circular gravel routes in the Gaylordsville area?
Yes, several routes are designed as loops. For example, the Housatonic River – Bulls Bridge loop from Wingdale offers a 54.5 km circular ride, and the Housatonic River – Class IV unmaintained fun loop from Kent is a moderate 30.6 km option.
What is the best time of year for gravel biking in Gaylordsville?
The region is particularly beautiful in the fall when autumn leaves transform the scenery, offering superb views along trails like the River Trail. Spring and summer also provide pleasant conditions for riding, though checking local weather is always recommended.
Are there any routes that pass by Lake Waramaug State Park?
Yes, the Lake Waramaug State Park – River Trail loop from New Milford is a 63.5 km route that incorporates the state park, offering opportunities for a break by the lake.
What do other gravel bikers say about the trails in Gaylordsville?
Over 40 gravel bikers have explored Gaylordsville's varied terrain using komoot. Riders often appreciate the challenging routes, scenic river views, and the network of well-maintained dirt roads that define the area's gravel biking experience.
Are there any routes that include the Tracy Road Gravel Route?
Yes, the extensive River Trail – Tracy Road Gravel Route loop from New Milford is a difficult 126.2 km path that specifically incorporates the designated Tracy Road Gravel Route.
What is the difficulty level of most gravel trails in Gaylordsville?
Most of the gravel trails around Gaylordsville are rated as difficult, featuring significant elevation gain and longer distances. There is also a moderate option, the Housatonic River – Class IV unmaintained fun loop from Kent, for those seeking a slightly less strenuous ride.
Can I find routes that feature both the River Trail and Bulls Bridge?
Absolutely. The River Trail – Bulls Bridge loop from New Milford is a challenging 112.8 km route that combines both the scenic River Trail and the historic Bulls Bridge.
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