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Gravel rides
United States
Vermont

Windham County

The best gravel rides in Windham County

5.0

(1)

113

riders

30

rides

Gravel biking in Windham County, Vermont, offers a diverse landscape characterized by extensive trail networks, dense forests, and rolling hills. The region features a mix of crushed gravel paths, dirt roads, and class 4 roads, providing varied terrain for cyclists. Riders can expect significant elevation changes across the county, with routes often traversing valleys and ascending into higher elevations. This area provides a robust setting for gravel biking adventures.

Best gravel bike trails in Windham County

  • The most popular gravel…

Last updated: July 11, 2026

15

riders

#1.

Halifax Village Center – Green River Covered Bridge loop from Bonnyvale Environmental Education Center

59.0km

04:14

1,310m

1,310m

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

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Hard

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

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

Hard

Hard gravel ride. Very good fitness required. You may need to push your bike for some segments of this route.

Hard

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

Hard
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Popular around Windham County

Gravel biking around Brattleboro

Gravel biking around Londonderry

Gravel biking around Algiers

Gravel biking around West Dummerston

Gravel biking around Putney

Roundabout Brattleboro — a charming challenge in the New England countryside

Hiking in Windham County

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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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Natalie
February 6, 2024, Lyons Pond

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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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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Natalie
November 29, 2023, Lyons Pond

Lyons Pond can be seen glistening between the tall pines trees. Many years ago, ice from the pond was stored in icehouses 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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great place

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mhzhao
September 20, 2021, Halifax Village Center

A picturesque crossroads where you’ll find all the inhabitants’ mailboxes lined up in the middle, overlooking a picture perfect New England little white church.

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All the town’s mailboxes in one place

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Frequently Asked Questions

How many gravel bike trails are available in Windham County?

Windham County offers a robust selection of over 25 gravel bike trails. These routes cater to various skill levels, with a significant number of challenging options for experienced riders.

What kind of terrain can I expect on gravel bike trails in Windham County?

You can expect a diverse landscape featuring extensive trail networks, dense forests, and rolling hills. The routes often combine crushed gravel paths, dirt roads, and class 4 roads, providing varied terrain with significant elevation changes as you traverse valleys and ascend into higher elevations.

Are there any moderate gravel biking routes for less experienced riders?

Yes, while many routes are challenging, there are moderate options available. For instance, the Gravel loop from Stratton Mountain is a moderate 25.1-mile ride with over 400 feet of elevation gain. Another moderate choice is the Weston Old Mill Museum loop from Weston, covering 16.2 miles with about 315 feet of climbing.

What are some notable landmarks or natural attractions I might see along the gravel routes?

Windham County's gravel routes often pass by beautiful natural features and landmarks. You might encounter scenic spots like Lowell Lake or the impressive Hamilton Falls. Several routes also offer views of prominent peaks such as Stratton Mountain, Mount Olga, and Haystack Mountain.

What do other gravel bikers say about the trails in Windham County?

The gravel biking experience in Windham County is highly regarded by the komoot community, holding an average rating of 5.0 stars. Riders often praise the challenging terrain, the beauty of the dense forests, and the significant elevation changes that make for rewarding adventures.

Are there any long-distance gravel loops in the area?

Absolutely. For a longer ride, consider the Townshend Reservoir loop from Stratton Mountain, which is a 45.2-mile trail leading through forested areas and past the reservoir. Another substantial option is the Weston Old Mill Museum – Morgan Hill loop from Hapgood Pond, a difficult 77.4-mile route with over 1300 meters of climbing.

What is a 'Class 4 road' in Vermont, and how does it affect gravel biking?

In Vermont, a 'Class 4 road' refers to a public road that is not maintained by the town. These roads can vary greatly in condition, from relatively smooth dirt tracks to very rough, rocky, or muddy paths that may be impassable by regular vehicles. For gravel biking, Class 4 roads often provide the most adventurous and challenging terrain, sometimes requiring wider tires or even a mountain bike, as mentioned in regional research for similar areas.

When is the best time of year for gravel biking in Windham County?

The best time for gravel biking in Windham County is typically from late spring through early fall. Spring can bring 'mud season' due to snowmelt, making some Class 4 roads very challenging. Fall offers beautiful foliage and cooler temperatures, while summer provides warm weather, though some routes may be dusty. Always check local conditions before heading out.

Are there any gravel routes that pass through or near covered bridges?

Yes, you can experience the charm of covered bridges on several routes. The Halifax Village Center – Green River Covered Bridge loop from Bonnyvale Environmental Education Center and the Green River Covered Bridge – Halifax Village Center loop from Franklin Dam both feature the historic Green River Covered Bridge, offering scenic views and a touch of local history.

What are the typical elevation gains on gravel rides in Windham County?

Gravel rides in Windham County are known for significant elevation changes. Even moderate routes can have several hundred feet of climbing, while difficult routes frequently feature over 1,000 meters (approximately 3,300 feet) of elevation gain. For example, the Halifax Village Center – Green River Covered Bridge loop has over 4,200 feet of elevation gain.

Is Windham County suitable for family-friendly gravel biking?

While many routes in Windham County are rated difficult, there are moderate options that might be suitable for families with older, more experienced children. For younger families or beginners, it's best to look for shorter, less hilly sections of trails or dedicated rail trails if available, as the region is characterized by significant elevation changes.

Are there any routes that start or end near popular towns or villages?

Yes, some routes are conveniently located near towns. For instance, the Weston Old Mill Museum loop from Weston starts and ends in Weston, offering access to local amenities. Other routes might start near places like Stratton Mountain, providing options for pre- or post-ride activities.

Most popular routes in Windham County

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Didn’t find what you were looking for?

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

PutneyWest DummerstonLondonderryAlgiersBrattleboro

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