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Routes
Cycling routes
United States
Vermont

Windham County

The best cycling routes in Windham County

4.8

(8)

112

riders

35

rides

Touring cycling routes in Windham County traverse a landscape characterized by rolling hills, picturesque river valleys, and extensive forests. The region features the West River and Connecticut River systems, providing scenic routes with gentle inclines. Parts of the Green Mountain National Forest contribute to the area's natural grandeur, offering wooded paths. Cyclists can also experience views of mountains like Black Mountain and Stratton Mountain.

Best touring cycling routes in Windham County

  • The most popular touring cycling route is Black Mountain…

Last updated: April 30, 2026

7

riders

#1.

Black Mountain Trailhead – West River loop from Brattleboro

24.9km

01:40

200m

200m

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

5.0

(2)

6

riders

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

5.0

(2)

6

riders

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

5.0

(1)

3

riders

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Popular around Windham County

Cycling around Bellows Falls

Cycling around South Londonderry

Cycling around Brattleboro

Cycling around Saxtons River

Cycling around Grafton

Cycling around West Brattleboro

Cycling in Fort Dummer State Park

Cycling around Algiers

Cycling around Londonderry

Cycling around Westminster Village

Other adventures in Windham County

Roundabout Brattleboro — a charming challenge in the New England countryside

Cycling Collection by

mhzhao

Tips from the Community

alsaman
August 26, 2025, Green River Covered Bridge

There is a small green space near bridge that is a great place to stop for a snack or lunch.

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AverieOutside
February 6, 2024, Hapgood Pond

Hapgood Pond is a 12-acre pond that is 12 feet deep at its deepest point. This pond is within a recreation area of the same name. The recreation area has a campground, restrooms, picnic tables, and a swimming beach.

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Jamie S.
December 30, 2023, The Mill Pond

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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The trail is a pleasant, peaceful hike through the woods along a number of waterfalls.

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The Native Americans of the region used to call the West River "Wantastiquet" which means "waters of the lonely way”. The Wantastiquet Trail is connected to both the mountains and the West River. This path was an important link that connected Fort Drumner and the Green Mountains.

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Lisa
October 12, 2023, Mirror Lake

A small, pretty lake just off the Valley Trail — your reward for a little bit or a little of walking, depending on where you started the trail.

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Lisa
October 12, 2023, Molly Stark statue

This statue honors Elizabeth Page "Molly" Stark, the wife of General John Stark, who won the Battle of Bennington during the American Revolutionary War. Molly herself is said to have been a staunch, fierce, and devoted woman during the difficult times of war.

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The trailhead has a small gravel lot, but the trail is not heavily trafficked so you are very likely to find parking space.

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Frequently Asked Questions

How many touring cycling routes are available in Windham County?

Windham County offers a diverse network of over 30 touring cycling routes. These routes cater to various skill levels, with an even split between moderate and difficult options.

What kind of terrain can I expect on touring cycling routes in Windham County?

You can expect a varied landscape characterized by rolling hills, picturesque river valleys, and extensive forests. Routes often feature views of rivers like the West River and Connecticut River, and mountains such as Black Mountain and Stratton Mountain. Some paths are paved, while others include unpaved segments, offering a mix of surfaces.

Are there any easy touring cycling routes suitable for beginners in Windham County?

While many routes are moderate, Windham County's network is generally accessible. For a moderate ride with scenic views, consider the Grafton Road loop from Simpsonville, which covers 33.5 km with manageable elevation.

What are some challenging touring cycling routes for experienced riders?

For experienced riders seeking a challenge, Windham County offers several difficult routes with significant elevation gains. The Deerfield River – Molly Stark statue loop from Mt Mills West Picnic Area is a demanding 67.7 km route with nearly 1000 meters of ascent. Another option is the Williams River State Forest loop from Grafton, a 36.2 km difficult route through forested areas.

What natural features or landmarks can I see along the touring cycling routes?

Windham County's routes often pass by beautiful natural features and landmarks. You might encounter rivers, forests, and views of mountains like Stratton Mountain and Black Mountain. Some routes also feature charming covered bridges and serene ponds, such as the Bowles Pond – Worrall Covered Bridge loop from Saxtons River.

Are there any circular touring cycling routes in Windham County?

Yes, many of the touring cycling routes in Windham County are designed as loops, allowing you to start and end at the same point. Examples include the The Mill Pond – Hapgood Pond loop from Londonderry and the Canoe Brook Nature Preserve loop from Beatrice Aiken Preserve.

What do other touring cyclists enjoy most about cycling in Windham County?

The touring cycling routes in Windham County are highly rated by the komoot community, with an average score of 4.8 stars from 8 reviews. Cyclists often praise the region's scenic beauty, the variety of terrain, and the peaceful atmosphere of the river valleys and forest paths.

Are there any routes that pass by waterfalls?

While not directly on every touring cycling route, the region is home to natural attractions like Hamilton Falls. You can plan your cycling tour to include a visit to such highlights, often accessible via short detours from main routes.

What is the best time of year to go touring cycling in Windham County?

The warmer months are particularly excellent for touring cycling in Windham County, offering pleasant weather to enjoy the scenic routes. The region's natural beauty, with its rivers, mountains, and forests, is vibrant during spring, summer, and fall. While trails adapt for winter sports, cycling is best enjoyed outside of the snowy season.

Are there family-friendly touring cycling options in Windham County?

Many routes in Windham County are suitable for various skill levels, and some offer mostly paved surfaces, making them more accessible for families. Look for routes with gentle inclines and shorter distances, often found along river valleys, to ensure a comfortable experience for all ages.

Where can I find parking for touring cycling routes in Windham County?

Many touring cycling routes in Windham County begin near towns or designated trailheads, where parking is typically available. For example, routes like the Bike loop from Stratton Mountain would likely have parking facilities near the resort area.

Can I find routes that go through charming villages?

Yes, Windham County's cycling network includes routes that traverse through charming villages. The Halifax Village Center – Green River Covered Bridge loop from Bonnyvale Environmental Education Center, for instance, takes you through local communities and past historic features.

Most popular routes in Windham County

Hiking in Windham County

Most popular attractions in Windham County

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Didn’t find what you were looking for?

Check out more Cycling routes throughout Windham County below and find the perfect route in your destination.

Westminster VillageChimney HillFort Dummer State ParkPutneyWest BrattleboroGraftonSouth LondonderryWest DummerstonLondonderryBellows FallsWilmingtonSaxtons RiverJamaicaAlgiersBrattleboro

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