4.6
(13)
578
riders
57
rides
Road cycling routes in Windham County traverse diverse landscapes, from the rolling hills and river valleys of Vermont and Connecticut to the mountainous terrain of the Catskills in New York. The region features a mix of paved and unpaved surfaces, offering varied elevation gains suitable for different skill levels. Cyclists can explore scenic rural byways, historic covered bridges, and routes alongside rivers and ponds. This varied topography provides options for both leisurely rides and more challenging ascents.
Last updated: April 30, 2026
5.0
(1)
13
riders
48.2km
02:18
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
17
riders
31.9km
01:29
390m
390m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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8
riders
73.6km
03:51
1,300m
1,300m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
10
riders
40.6km
02:00
600m
600m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
45.6km
02:07
580m
580m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
42.2km
01:53
400m
400m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
10
riders
49.8km
02:34
830m
830m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
53.1km
02:17
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
55.6km
02:31
600m
600m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
7
riders
28.4km
01:27
370m
370m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Popular around Windham County

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Lyons Pond can be seen glistening between the tall pine trees. Many years ago, ice from the pond was stored in ice houses for use in food preservation during the summer. The ice was packed into the houses with sawdust and it was surprisingly effective. If done well, it could remain frozen for several years.
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A place of tranquility. Weatherhead Hollow pond is the ideal place to relax yourself and embrace some of the nature finest gifts: the soothing of the mind with smooth sound. The pond has a parking on the south end, which allows you to bring your non-motor sailing vehicle and float on its waters.
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A place of tranquility. Weatherhead Hollow pond is the ideal place to relax yourself and embrace some of nature's finest gifts: the soothing of the mind with smooth sound. The pond has parking on the south end, which allows you to bring your non-motor sailing vehicle and float on its waters. The views of the mountains and the forest are the ones you desire to find on your probably chilled bike touring adventure. Don't miss the opportunity to immortalize the scene.
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Feel yourself hovering over Sawyer Pond as you fly on Old Vernon Road. The brown fallen leaves of autumn make this place picture-worthy.
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Cushman Park, being right next to the Darwin Scott Wildlife Management Area, provides a green space for the public to enjoy. The park was donated back in 1908, and the adjacent Darwin Scott Wildlife Management Area provides 27.92 acres of explorable space. Cushman Park is an important part of the community, with local events and art displays happening here quite often.
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Sawyer Pond lies on both sides of Old Vernon Road. This is a pretty spot to ride by because you are surrounded by water on both sides.
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Cushman Park, being right next to the Darwin Scott Wildlife Management Area, provides a green space for the public to enjoy. The park was donated back in 1908, and the adjacent Darwin Scott Wildlife Management Area provides 27.92 acres of explorable space. Cushman Park is an important part of the community, with local events and art displays happening here quite often.
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The Mill Pond is a small pond off of the scenic West River in Londonderry, Vermont. It is just east of downtown Londonderry where you can get a bite to eat on your ride.
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Windham County offers a diverse range of road cycling routes across Vermont, Connecticut, and New York. You'll find everything from scenic river valleys and rolling hills to challenging mountainous terrain. Routes feature a mix of paved and unpaved surfaces, catering to various skill levels and preferences.
Yes, Windham County has options for all skill levels. While many routes offer moderate to difficult challenges, there are also easier paths. For example, the Roadbike loop from Dutton Pines State Forest Park is a moderate 28.4 km route that provides a good experience without extreme difficulty. The region's varied topography ensures you can find a comfortable ride.
Windham County is rich in natural beauty. In Vermont, you can enjoy routes with views of the West River and Black Mountain, or explore historic covered bridges like the Worrall Covered Bridge. Connecticut offers rides along the East Coast Greenway with rolling hills and farms, and the town of Putnam features a beautiful waterfall and river parks. In New York's Catskills, the Windham Path provides views of the Batavia Kill Stream and northern Catskills, while other routes offer glimpses of riffles and waterfalls. Consider the Mirror Lake loop from Lake Raponda for picturesque lake views.
Yes, for cyclists seeking longer distances, Windham County provides several options. The Snow Lake – Mill Pond loop from Drop Off Area is a challenging 73.6 km trail. Other routes like the Weatherhead Hollow Pond – Cushman Park loop from Brattleboro cover over 55 km, offering extended rides through varied landscapes.
While cycling in Windham County, you can encounter several interesting landmarks and natural attractions. In Vermont, routes might pass by Stratton Mountain, Black Mountain, or Lowell Lake. You might also spot Hamilton Falls. The region is also known for its charming village settings and historic covered bridges, particularly in Vermont and along the Windham Path in New York.
The road cycling routes in Windham County are highly regarded by the komoot community, with an average rating of 4.6 stars from over 8 reviews. Cyclists often praise the diverse terrain, from rolling hills to challenging ascents, and the scenic beauty of the river valleys, lakes, and historic features.
Yes, many of the road cycling routes in Windham County are designed as loops, offering convenient circular journeys. Examples include the popular Lyons Pond – The Mill Pond loop from Lot C, the The Mill Pond loop from Lot C, and the Roadbike loop from Saxtons River, allowing you to start and finish at the same point.
The best time for road biking in Windham County generally spans from spring through fall. During these seasons, the weather is typically mild, and the landscapes are vibrant. Spring brings fresh greenery, summer offers warm days, and fall showcases stunning foliage, especially in Vermont and the Catskills. Winter cycling can be challenging due to snow and ice, particularly in higher elevations.
Absolutely. Windham County features several routes that offer picturesque views of ponds and lakes. The Lyons Pond – The Mill Pond loop from Lot C and the Mirror Lake loop from Lake Raponda are excellent choices for enjoying waterside scenery. You can also find routes near Lowell Lake.
There are over 50 road cycling routes documented in Windham County, offering a wide array of choices for cyclists. These routes range in difficulty from moderate to difficult, ensuring options for various experience levels.
Yes, if you're looking for a challenge, Windham County's mountainous terrain, particularly in the Catskills region of New York and parts of Vermont, offers routes with significant elevation gains. Routes around Windham Mountain in New York and the Williams River State Forest loop from Grafton in Vermont provide substantial ascents and descents for advanced cyclists. The Snow Lake – Mill Pond loop from Drop Off Area, for instance, features over 1200 meters of elevation gain.
Yes, in Windham County, Connecticut, the Windham Recreation Department organizes group bike rides on the Airline Trail. This can be a great way to explore scenic routes and connect with other cyclists. You can find more information on their official website: windhamct.gov.


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