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Routes
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United States
Vermont

Windham County

The best traffic-free bike rides in Windham County

4.8

(8)

112

riders

15

rides

No traffic touring cycling routes in Windham County traverse a landscape characterized by diverse terrain, including river valleys, rolling hills, and forested areas. The region features prominent natural features such as the West River and Connecticut River, providing scenic backdrops for cycling. Many routes offer a mix of paved surfaces and varying elevation changes, catering to different fitness levels. This area is known for its picturesque views and a network of trails suitable for touring cyclists seeking car-free paths.

Best…

Last updated: May 11, 2026

7

riders

#1.

Black Mountain Trailhead – West River loop from Brattleboro

24.7km

01:40

190m

190m

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
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Popular around Windham County

Traffic-free bike rides in Fort Dummer State Park

Traffic-free bike rides around Brattleboro

Roundabout Brattleboro — a charming challenge in the New England countryside

Traffic-free bike rides in Windham County

Traffic-free bike rides in Windham County

Other adventures in Windham County

Roundabout Brattleboro — a charming challenge in the New England countryside

Cycling Collection by

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

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Zachary
September 22, 2023, West River

The West River flows south along the path to Brattleboro, where it merges with the Connecticut River at the Vermont - New Hampshire border. The trail here is a nice scenic bike path with views of the river and Black Mountain to the north.

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Frequently Asked Questions

How many no-traffic touring cycling routes are available in Windham County?

Windham County offers a good selection of no-traffic touring cycling routes, with 15 distinct tours available. These routes cater to various fitness levels, ensuring a suitable option for most cyclists.

What kind of terrain and difficulty can I expect on the no-traffic touring cycling routes in Windham County?

The no-traffic touring cycling routes in Windham County feature varied terrain. While many segments are paved, you can expect a mix of gentle ascents and significant climbs. The routes are categorized by difficulty: 7 are considered moderate, and 8 are difficult, requiring very good fitness. For example, the Black Mountain Trailhead – West River loop from Brattleboro is a moderate ride, whereas the Halifax Village Center – Green River Covered Bridge loop from Bonnyvale Environmental Education Center is a difficult one.

Are there any family-friendly no-traffic touring cycling routes in Windham County?

While there are no routes specifically marked as 'easy' in this selection, several moderate routes could be suitable for families with good cycling experience. The Black Mountain Trailhead – West River loop from Brattleboro is a moderate ride, mostly on paved surfaces, which might be a good option for families looking for a scenic, less challenging experience.

What are some scenic highlights or natural features I can see along these routes?

Windham County's no-traffic routes offer stunning natural beauty. You can enjoy picturesque views of the West River and Connecticut River, and many routes pass through lush forests. Notable natural features include Lowell Lake, and various mountain views from peaks like Stratton Mountain and Mount Olga. The region is also known for its charming covered bridges.

Are there any circular no-traffic touring cycling routes available?

Yes, many of the no-traffic touring cycling routes in Windham County are circular, offering convenient starting and ending points. Examples include the Grafton Road loop from Simpsonville, the The Mill Pond – Hapgood Pond loop from Londonderry, and the Canoe Brook Nature Preserve loop from Beatrice Aiken Preserve.

What is the best time of year to enjoy no-traffic touring cycling in Windham County?

The best time to enjoy no-traffic touring cycling in Windham County is typically during the spring, summer, and fall months. Spring offers fresh greenery, summer provides warm weather, and fall showcases spectacular foliage. Always check local weather conditions before heading out, especially during shoulder seasons.

What do other touring cyclists enjoy most about the no-traffic routes in Windham County?

The no-traffic 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 scenic landscapes, the quiet roads, and the diverse terrain that offers both challenging climbs and enjoyable stretches.

Are there any waterfalls accessible from the no-traffic touring cycling routes?

Yes, for those interested in natural attractions, Hamilton Falls is a notable waterfall in Windham County that can be explored. While not directly on every cycling route, it's a significant highlight in the region worth visiting.

Where can I find parking for these no-traffic touring cycling routes?

Many of the popular cycling routes in Windham County, such as the West River Trail, offer designated parking areas for access. For specific routes, it's advisable to check the individual tour details on komoot, as parking information is often provided at the trailhead or starting point.

Are dogs allowed on the no-traffic touring cycling routes?

While many outdoor areas in Windham County are dog-friendly, specific regulations can vary by trail or park. It's generally recommended to keep dogs on a leash and ensure they are well-behaved. Always check the specific rules for each route or trail system before bringing your dog along.

Are there any routes that offer views of mountains or rivers?

Absolutely. Many no-traffic touring cycling routes in Windham County are designed to showcase the region's natural beauty. The West River Trail, for instance, offers continuous views of the West River and Black Mountain. Other routes provide vistas of the Connecticut River and various mountain peaks like Stratton Mountain and Mount Olga.

Most popular routes in Windham County

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Fort Dummer State ParkBrattleboro

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