5.0
(1)
178
riders
34
rides
Road cycling around Gaylordsville, situated in Litchfield County, Connecticut, offers diverse terrain characterized by rolling hills, scenic river valleys, and tranquil country roads. The region provides an idyllic backdrop for cycling, with routes often paralleling the Housatonic River and passing through picturesque rural landscapes. Cyclists can expect a mix of moderate climbs and flatter sections, making it suitable for various fitness levels.
Last updated: October 29, 2026
8
riders
56.5km
02:50
790m
790m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
59.1km
02:36
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

10
riders
47.3km
02:11
550m
550m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
35.9km
01:35
330m
330m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
35.1km
01:29
290m
290m
Easy road ride. Mostly well-paved surfaces and easy to ride.
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Disbrow Pond is a small body of water just off the side of Sawmill Road. You get a pretty great view from the bridge crossing over the water, but you can hop off the bike and go down next to the water if you pull into the entrance on the north side of the reservoir.
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Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.
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Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.
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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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Opportunity to have a decent meal along this route. Friendly folks refill water and it has a proper washroom as well. In general Kent is a good stop to refill or rest before heading further as supply station might become sparse.
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Road cycling around Gaylordsville, located in Litchfield County, Connecticut, is characterized by a mix of rolling hills, scenic river valleys, and tranquil country roads. You'll find routes that often parallel the Housatonic River, offering picturesque rural landscapes. The area provides a diverse experience with both moderate climbs and flatter sections, suitable for various fitness levels.
There are over 25 road cycling routes around Gaylordsville available on komoot, catering to different preferences and skill levels. These routes have been explored by more than 140 road cyclists in the community.
Yes, while many routes are moderate, there are options for beginners. The region's quiet country roads and sections of the New Milford River Trail (though some parts are packed dirt/crushed stone) can offer a gentler experience. For a moderate but scenic ride, consider the Hatch Pond – Leonard Pond loop from Sherman, which covers 22.8 miles (36.7 km) with manageable elevation.
You can encounter several interesting landmarks and natural features. The historic Bulls Bridge, a covered wooden bridge over the Housatonic River, is a popular sight, often featured on routes like the Bulls Bridge loop from South Kent. The majestic Housatonic River itself provides continuous scenic views, and you might also pass by Lake Waramaug State Park, a beautiful spot for a break.
The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the picturesque rural landscapes, the tranquility of the country roads, and the diverse terrain that offers both challenging climbs and scenic, flatter sections. The presence of historic landmarks like Bulls Bridge also adds to the appeal.
Yes, Gaylordsville is part of a broader network that includes longer routes. For example, the Fife 'n Drum Restaurant & Inn loop from Sherman is a moderate 36.7 miles (59.1 km) path exploring the quiet country roads of Litchfield County. The Squantz Pond – Squantz Pond loop from Candlewood Mountain is another substantial route at 35.1 miles (56.5 km).
While many road cycling routes in the area involve rolling hills, some sections of the New Milford River Trail offer a more accessible, flatter experience, though parts are unpaved. For road biking with families, look for routes with less traffic and gentler gradients. Always check route details for surface type and elevation before heading out with children.
The spring, summer, and especially autumn months are ideal for road cycling in Gaylordsville. Autumn is particularly beautiful due to the changing New England foliage. While some routes may be accessible in winter, conditions can be challenging due to snow and ice, so it's best to check local weather and trail conditions.
Yes, the Litchfield County area, including towns near Gaylordsville like Kent and New Milford, offers various cafes and local establishments where cyclists can stop for refreshments. While specific cafes directly on every route aren't listed, planning your ride through or near these towns will provide opportunities for breaks.
Parking for cyclists is generally available at various access points for trails and in nearby town centers. For routes that utilize the New Milford River Trail, look for parking areas near sections like Sega Meadows Park or other designated trailheads. When starting a loop route, parking is often available in the starting town or at public access points.
Many of the road cycling routes around Gaylordsville are designed as loops, allowing you to start and end at the same point. Examples include the Squantz Pond – Squantz Pond loop from Candlewood Mountain and the Bulls Bridge loop from South Kent, which are popular choices for their scenic circular paths.
Yes, the New Milford River Trail Greenway, which connects to Gaylordsville, also overlaps with the Western New England Greenway (U.S. Bike Route 7). This broader network provides connectivity for cyclists, utilizing existing trails and less-traveled roadways for safe cycling.


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