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Road cycling around Bigelow Corners, a location within Connecticut, features routes that traverse extensive forest networks and areas around lakes and ponds. The terrain includes varied elevation changes, from gentle gradients to more challenging climbs. Cyclists can expect to encounter old forests, streams, and natural features characteristic of the region's undeveloped landscapes. The area offers a mix of paved surfaces and well-maintained roads suitable for road bikes.
Last updated: June 29, 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…
13
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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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.
4
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3
riders
The "Lovers Landing Bridge – White Pond loop from Cranberry Mountain Wildlife Management Area" presents a unique challenge for road cyclists, traversing 29.3 miles (47.2 km) with a substantial 2025…
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Popular around Bigelow Corners
This paved rail trail traverses two counties in New York — you can bike more than 28 miles on it if you go from end to end. This particular section passes through a sort of wetland land — keep an eye out for birds!
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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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It's along the rail trail. No fishing and no swimming from the trail side.
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Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
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This nice pond is very popular with swimming, fishing, and ice fishing enthusiasts.
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Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
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There are over 20 road cycling routes around Bigelow Corners, offering a variety of options for different skill levels and preferences. The komoot community has explored these routes over 350 times.
Road cycling around Bigelow Corners features routes that traverse extensive forest networks and areas around lakes and ponds. The terrain includes varied elevation changes, from gentle gradients to more challenging climbs, with a mix of paved surfaces and well-maintained roads suitable for road bikes.
Yes, Bigelow Corners offers several easier routes. While specific family-friendly routes aren't detailed, there are 5 routes classified as 'easy' within the area. These routes generally have less elevation gain and shorter distances, making them more accessible.
A popular moderate route is the Maybrook Trailway – Whaley Lake loop from Putnam Lake, a 36.6-mile trail with over 1,700 feet of elevation gain. Another favorite is the Maybrook Trailway – Maybrook Trailway loop from Cranberry Mountain Wildlife Management Area, a 26.6-mile path with over 1,100 feet of elevation gain.
For experienced cyclists seeking a challenge, the Squantz Pond – Bulls Bridge loop from New Fairfield is a difficult 54.7-mile trail with over 3,300 feet of elevation gain, typically completed in about 4 hours and 5 minutes. There are 2 routes classified as 'difficult' in the region.
The region's extensive forest networks and lakes suggest that spring, summer, and fall would offer the most pleasant conditions for road cycling. Spring brings fresh greenery, summer offers warm weather, and fall provides vibrant foliage. Winter activities like cross-country skiing and ice fishing are popular in the broader Bigelow Hollow State Park, but road cycling might be limited by snow and ice.
While specific parking locations for each route are not detailed, many routes, such as the Maybrook Trailway loop and the Lovers Landing Bridge – White Pond loop, start from the Cranberry Mountain Wildlife Management Area, which typically offers parking facilities for outdoor activities.
Road cycling routes in Bigelow Corners often pass through old forests, alongside streams, and near various lakes and ponds, including Bigelow Pond and Mashapaug Lake. You can also expect to encounter intriguing rock formations and diverse landscapes characteristic of the region's undeveloped forest expanse.
Yes, many of the routes are designed as loops, offering a circular journey. Examples include the Maybrook Trailway – Whaley Lake loop, the Maybrook Trailway – Maybrook Trailway loop, and the Squantz Pond – Bulls Bridge loop, allowing you to start and end at the same point.
The area is highly rated by the komoot community, with an average score of 4.3 stars from over 15 reviews. Cyclists often praise the varied terrain, the extensive forest networks, and the scenic beauty around the lakes and ponds, providing a diverse and engaging riding experience.
For those looking for longer rides, the Squantz Pond – Bulls Bridge loop from New Fairfield is a substantial 54.7-mile route. Another option is the Lovers Landing Bridge – White Pond loop from Cranberry Mountain Wildlife Management Area, which covers 29.3 miles.


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