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Running Trails
United States
Vermont

Windham County

The best running trails in Windham County

4.0

(1)

117

runners

43

runs

Jogging routes in Windham County traverse a diverse landscape characterized by woodlands, rivers, and varied terrain. The region, often referred to as "the Quiet Corner" of Connecticut, offers numerous opportunities for running amidst natural features. State parks and conservation areas provide a network of trails suitable for different preferences. These paths often follow former railroad lines or wind through forests and along waterways.

Best jogging routes in Windham County

  • The most popular jogging route is Wantastiquet Mountain Trail, a…

Last updated: June 28, 2026

3

runners

#1.

Wantastiquet Mountain Trail

6.19km

01:04

290m

290m

Embark on a challenging jogging adventure along the Wantastiquet Mountain Trail, a difficult 3.8-mile (6.2 km) route that climbs 964 feet (294 metres). This journey, typically completed in about 1…

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Hard

Embark on a moderate jogging experience along the Fort Hill Recreational Rail Trail, a 6.1 miles (9.7 km) route that offers varied terrain and scenic views. As you jog, you…

Moderate
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Jog along the picturesque Connecticut River on the Wantastiquet Mountain Natural Area River Trail, where continuous water views accompany you. This easy 2.4-mile (3.9 km) route follows an old dirt…

Easy

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

Hard

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

Moderate

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

Hard

5

runners

11.3km

01:11

130m

130m

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

Moderate

4

runners

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

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

Hard

4.0

(1)

3

runners

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

Moderate
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Popular around Windham County

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Running Trails in Fort Dummer State Park

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Running Trails around Chimney Hill

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Tips from the Community

mtm05005
October 17, 2023, Fort Hill Recreational Trail

The Fort Hill Recreational Trail is a 9-mile long multiuse trail that is built along the old Boston and Maine Railroad. The surface is crushed stone and gravel and is a great place for a quiet run.

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

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Clearing that gives a great view of the mountains and valleys in the area. It is a popular spot, so there is a good chance you will see others at the viewpoint.

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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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It's a nice challenge for any hiker with a rewarding view at the end.

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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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A nice place for a hike. Some great views during the hike, but to the get to the best viewing spot is quite a hike.

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Start der Tour mit Wasserfall/Start of the tour with waterfall

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Frequently Asked Questions

How many running routes are available in Windham County?

Windham County offers a wide selection of running routes, with over 40 trails available for you to explore. These routes cater to various preferences, from easy jogs to more challenging runs.

What is the overall rating for running trails in Windham County?

The running routes in Windham County are highly regarded by the komoot community, boasting an average rating of 4.0 stars. Runners frequently praise the scenic beauty and diverse terrain.

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

Windham County's running routes offer a diverse landscape, from flat, well-maintained paths like sections of the Air Line State Park Trail to more challenging trails with significant elevation changes. You'll find paths winding through woodlands, along rivers, and leading to scenic overlooks, providing a varied experience for all runners.

Are there any long-distance running trails in Windham County?

Yes, for those seeking longer runs, Windham County has several options. The Mill Pond loop from Winhall Town Forest is a notable example, covering approximately 16.5 km (10.3 miles). The Air Line State Park Trail also offers extensive mileage, with sections stretching over 50 miles, providing ample opportunity for long-distance training.

Are there any circular running routes in Windham County?

Yes, many routes in Windham County are designed as loops, offering a convenient way to start and finish your run at the same point. For example, the Haystack Mountain loop from Chimney Hill and the Mill Pond loop from Winhall Town Forest are popular circular options.

Are the running trails in Windham County suitable for families or strollers?

Yes, Windham County offers family-friendly options. Trails like the Air Line State Park Trail and the Windham Path (as described in regional research) are often flat and well-maintained, making them suitable for families and some sections may be accessible with strollers. Always check specific route details for terrain and accessibility.

Can I bring my dog on the running routes in Windham County?

Many trails in Windham County are dog-friendly, allowing you to enjoy a run with your canine companion. It's always best to check local regulations for specific parks or trails, but generally, state parks and conservation areas welcome leashed dogs. Please remember to clean up after your pet.

What are some scenic viewpoints or natural features I can see while running in Windham County?

Windham County is rich in natural beauty. You can encounter stunning vistas from trails leading to cliff overlooks in places like Old Furnace State Park. Other routes feature picturesque rivers, such as the Natchaug River at Diana's Pool, and serene lakes like Lowell Lake. Several routes also offer views of prominent peaks like Haystack Mountain and Stratton Mountain.

Are there any easy running routes for beginners in Windham County?

Absolutely. Windham County has 4 easy running routes perfect for beginners or those looking for a relaxed jog. The Wantastiquet Mountain Natural Area River Trail, at 3.9 km, is a great option, often completed in about 25 minutes. Rail trails, like the Fort Hill Recreational Rail Trail, also provide relatively flat and consistent surfaces.

What is the best season for running in Windham County?

Windham County offers a beautiful backdrop for running throughout all four seasons. Spring brings lush greenery, summer provides warm weather for early morning or evening runs, and autumn showcases vibrant foliage. Even winter can be enjoyable for running, with trails offering a serene, snow-covered landscape, though conditions may vary and require appropriate gear.

Are there any running routes with significant elevation gain for a challenging workout?

Yes, for runners seeking a challenge, Windham County features several routes with significant elevation gain. The Wantastiquet Mountain Trail, for instance, includes over 290 meters of ascent, leading to rewarding views. Other difficult routes, such as the Dancing Bear – Mid Mountain Lodge loop from Stratton Mountain, offer even greater climbs.

Are there any cafes or pubs near popular running trails in Windham County?

While specific establishments vary by location, many towns and villages throughout Windham County, especially near state parks and popular trailheads, offer cafes and pubs where you can refuel after your run. Areas around the Air Line State Park Trail and other major recreational spots often have amenities nearby.

Most popular routes in Windham County

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Check out more Running Trails & Routes throughout Windham County below and find the perfect route in your destination.

Chimney HillFort Dummer State ParkWest BrattleboroJamaicaAlgiersBrattleboro

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