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Hikes
United States
Vermont
Windham County

West Brattleboro

Easy hikes and walks around West Brattleboro

4.9

(6)

112

hikers

21

hikes

Easy hiking trails around West Brattleboro offer access to a landscape characterized by conserved forests, rolling hills, and scenic river valleys. The region, part of Vermont's "Green Mountain State," features diverse terrain ranging from gentle riverside paths to trails winding through lush woodlands. These natural features provide varied opportunities for outdoor exploration on foot.

Best easy hiking trails around West Brattleboro

  • The most popular easy hiking route is Anne Stokes Loop Trail, a 2.1 miles (3.4 km) trail that…

Last updated: July 27, 2026

8

hikers

#1.

Anne Stokes Loop Trail

3.37km

01:03

120m

120m

The Anne Stokes Loop Trail offers a delightful blend of forest scenery and intriguing history within the Madame Sherri Forest. As you hike, you'll traverse diverse terrain, from gentle woodland…

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Easy

The West River Trail - Lower Section offers a delightful, easygoing escape along the West River in Southern Vermont. Following the historic bed of the former West River Railroad, this…

Easy
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The Little Black Mountain Trail offers a unique journey back in time, leading you through a desert landscape dotted with ancient petroglyphs. This easy hiking route is a short 0.6…

Easy

4.5

(2)

12

hikers

5.22km

01:46

260m

260m

The Black Mountain Loop Trail offers a delightful and accessible outdoor experience, perfect for a refreshing walk. This easy circular walk takes you through natural landscapes, providing a consistent and…

Easy

Wander through attractive forests and along the tranquil shores of Kilburn Pond on this delightful loop. The northern shore of Kilburn Pond is a real gem, especially when autumn colors…

Easy
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Tips from the Community

Zachary
October 17, 2023, Kilburn Pond

The pond is great for swimming and the edge is lined with large stones that are perfect for scrambling, picnicking, and enjoying the water.

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mtm05005
October 17, 2023, Kilburn Trailhead

Trailhead with parking that lets you choose whether to take the paths that bring you east to Pisgah State Forest or west to Daniels Mountain. In the high season it can get busy, so make sure to get there early to get a parking spot.

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Zachary
September 22, 2023, Black Mountain

The trees part to make way for outcroppings of stone at the summit which offer great views of the forest and north Brattleboro.

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You can park up off of Rice Farm Road. Parking is limited, but the trail is beautiful and includes many water features.

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The trail here is a beautiful forest path near an idyllic stream.

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Zachary
September 22, 2023, Madame Sherri House

The ruins of the Madam Sherri House. The ruins are truly special and well worth a visit. The main structure that remains is a spiraling triple-arched stone staircase fit for a storybook leading up to the stone bones of a mansion.

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Zachary
September 22, 2023, Wantastiquet Trailhead

There is a large packed gravel parking lot at the trailhead. You begin the trail by crossing a neat wooden bridge by a stone-walled pond.

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The bridge crossing is beautiful. From here the trail around the east side of the lake wanders through the forest, while the western trail is wider and hugs the shore.

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Frequently Asked Questions

How many easy hiking trails can I find in West Brattleboro?

West Brattleboro offers a good selection of easy hiking trails. There are 11 easy routes available, part of a larger network of 21 trails in the area, ensuring diverse options for a relaxed outdoor experience.

What kind of terrain can I expect on easy hikes in West Brattleboro?

Easy hikes in West Brattleboro feature diverse terrain, from gentle riverside paths along the West River to trails winding through lush woodlands and rolling hills. Many routes follow former railbeds, offering gradual elevation changes and varied surfaces like asphalt, crushed stone, dirt, and gravel.

Are there any easy loop trails in West Brattleboro?

Yes, West Brattleboro has several easy loop trails. Popular options include the Anne Stokes Loop Trail, which winds through forested areas, and the Black Mountain Loop Trail, leading through forested hills. For a slightly longer option, consider the Anne Stokes and Daniels Mountain Loop Trail.

What are the best trails for families with children?

For families, the West River Trail - Lower Section is an excellent choice. It follows the scenic West River on relatively flat terrain, making it suitable for relaxed walks. The Retreat Trails network also offers nature trails and footpaths through historic farmland, often with interpretive placards that can engage younger hikers.

Are there any dog-friendly easy trails in the area?

Yes, many trails in West Brattleboro are dog-friendly. The Bonnyvale Environmental Education Center (BEEC) offers 2 miles of trails across 100 acres of fields and forests where dogs are welcome. Always ensure your dog is leashed and follow local regulations.

What natural features or landmarks can I see on these easy hikes?

Easy hikes in West Brattleboro offer views of conserved forests, rolling hills, and the scenic Connecticut and West River valleys. You can spot large old sugar maples, spring wildflowers, and enjoy expansive views from places like Heifer Hill. The View of Vermont from Wantastiquet Mountain Stone Post offers panoramic vistas, and the Madame Sherri House is a notable historical site nearby.

What is the best time of year to go hiking in West Brattleboro?

West Brattleboro offers beautiful hiking experiences year-round. Spring brings wildflowers, while summer provides lush green landscapes. Fall is particularly spectacular with vibrant foliage. In winter, many of the same trails are suitable for peaceful snowshoeing.

What do other hikers enjoy most about hiking in West Brattleboro?

The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the region's diverse terrain, from gentle riverside paths to forested loops, and the opportunity to experience Vermont's natural beauty, especially the conserved forests and scenic river valleys.

Are there opportunities for birdwatching on easy trails?

Yes, West Brattleboro's diverse ecosystems make it excellent for birdwatching. The Whetstone Woods features a dedicated birding trail with interpretive signs. The Connecticut and West River systems are also prime locations for observing wildlife, including migratory birds, eagles, and various forest bird species, especially during spring and fall.

Are there any historical sites accessible via easy trails?

Yes, the Retreat Trails network, accessible from the Retreat Farm, winds through carriage roads originally established in the 1800s, offering an interpretive trail with placards detailing local history. Additionally, Fort Dummer State Park, Vermont's first permanent white settlement, has easy hiking paths within its historic grounds. The nearby Madame Sherri House is also a notable historical site.

What is the shortest easy trail available?

The shortest easy trail is the Little Black Mountain Trail, which is approximately 1 kilometer (0.6 miles) long. It's a quick and accessible option for a short walk.

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