4.9
(25)
836
riders
45
rides
Road cycling routes around Taylor Corners traverse a landscape characterized by rolling hills, scenic lakes, and a network of trails, including sections of the Maybrook Trailway. The region offers varied terrain suitable for road cyclists, with routes winding through areas like Cranberry Mountain Wildlife Management Area and past bodies of water such as Whaley Lake and Squantz Pond. Elevations vary, providing both moderate climbs and more challenging ascents. The area's roads and trails offer opportunities to explore the local natural…
Last updated: July 12, 2026
36
riders
Embark on a scenic road cycling adventure along the Maybrook Trailway loop, where you'll glide through quiet woodlands and past picturesque bodies of water like Whaley Lake. The route offers…
6
riders
44.9km
02:17
550m
550m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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4
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3
riders
25.8km
01:18
360m
360m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Taylor Corners
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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In summer, it is a great place for hiking, and in winter, when the lake is covered with ice, it is great for ice skating.
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This nice pond is very popular with swimming, fishing, and ice fishing enthusiasts.
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Great skies and good riding surface. Strong winds can be a challenge here.
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Taylor Corners offers a wide selection of road cycling routes, with over 40 routes available. These include options for various skill levels, from easy rides to more challenging ascents.
Road cycling routes around Taylor Corners are characterized by rolling hills, scenic lakes, and sections of converted rail trails like the Maybrook Trailway. You'll find varied terrain, offering both moderate climbs and more challenging ascents, winding through areas such as Cranberry Mountain Wildlife Management Area and past bodies of water like Whaley Lake and Squantz Pond.
Yes, Taylor Corners has several easy road cycling routes suitable for beginners. There are 9 routes specifically categorized as easy, providing a gentle introduction to the area's scenic beauty.
Absolutely. For experienced cyclists seeking a challenge, Taylor Corners offers 4 difficult routes. One such route is the Squantz Pond – Bulls Bridge loop from New Fairfield, which spans 54.7 miles (87.9 km) and features over 1000 meters of elevation gain.
Many road cyclists enjoy loop routes in Taylor Corners. A popular moderate option is the Maybrook Trailway – Whaley Lake loop from Putnam Lake, which covers 36.6 miles (58.9 km) and circles Whaley Lake. Another favorite is the Maybrook Trailway – Maybrook Trailway loop from Cranberry Mountain Wildlife Management Area, a 26.6-mile (42.8 km) moderate path following sections of the Maybrook Trailway.
Road cycling routes in Taylor Corners offer views of several natural attractions. You can ride along the Maybrook Trailway, pass by Parks Pond and Picnic Site, and cycle near Squantz Pond State Park and Squantz Pond, enjoying the scenic lake views.
Yes, for those who enjoy exhilarating descents, the Christ Church on Quaker Hill – Fantastic descent loop from Cranberry Mountain Wildlife Management Area is a moderate route that includes notable downhill sections.
The road cycling experience in Taylor Corners is highly rated by the komoot community, with an average score of 4.5 stars from over 20 reviews. Cyclists often praise the diverse terrain, including rolling hills and scenic lake views, as well as the well-maintained sections of converted rail trails like the Maybrook Trailway.
Many routes offer scenic points of interest. For example, the Lovers Landing Bridge – White Pond loop from Cranberry Mountain Wildlife Management Area takes you past Lovers Landing Bridge and White Pond, offering picturesque views along the way.
While specific conditions vary, the region's rolling hills and lake views are generally enjoyable during spring, summer, and fall. These seasons typically offer pleasant weather for exploring the diverse landscapes and trails, including the Maybrook Trailway and areas around Whaley Lake and Squantz Pond.
Many of the routes in Taylor Corners traverse areas with minimal traffic, especially those utilizing sections of the Maybrook Trailway or winding through natural areas like Cranberry Mountain Wildlife Management Area. This allows for a more peaceful and immersive cycling experience amidst the region's scenic beauty.


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