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Hikes
United States
Vermont
Windham County

Brattleboro

Easy hikes and walks around Brattleboro

4.9

(6)

108

hikers

24

hikes

Easy hiking trails around Brattleboro offer access to diverse landscapes, including conserved forests, rolling hills, and ridgelines. The region is characterized by its proximity to the Connecticut River Valley, providing varied terrain from riverside paths to elevated viewpoints. Hikers can explore a network of trails through woodlands, open meadows, and along former railbeds.

Best easy hiking trails around Brattleboro

  • The most popular easy hiking route is Black Mountain Loop Trail, a 3.2 miles (5.2 km) trail that takes about…

Last updated: June 23, 2026

7

hikers

#1.

Anne Stokes Loop Trail

3.37km

01:03

120m

120m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

4.5

(2)

12

hikers

5.22km

01:46

260m

260m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Popular around Brattleboro

Roundabout Brattleboro — a charming challenge in the New England countryside

Other adventures around Brattleboro

Roundabout Brattleboro — a charming challenge in the New England countryside

Cycling Collection by

mhzhao

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 are available around Brattleboro?

There are 11 easy hiking trails around Brattleboro, offering diverse options for exploring the region's natural beauty.

What kind of landscapes can I expect on easy hikes near Brattleboro?

Easy hikes around Brattleboro traverse a variety of landscapes, including conserved forests, rolling hills, and ridgelines offering views of the Connecticut River Valley. You'll find riverside paths, open meadows, and trails winding through woodlands.

Are there any easy loop trails for a circular walk?

Yes, several easy loop trails are available. The Black Mountain Loop Trail is a 3.2-mile path through a quiet forest. Another option is the Anne Stokes and Daniels Mountain Loop Trail, a 4.0-mile route that includes forested areas and some elevation gain. For a shorter option, consider the 1.3-mile loop around Sweet Pond State Park.

Which easy trails are suitable for families with children?

Many easy trails are family-friendly. The Kilburn Pond and John Summers Trail is a 3.0-mile route through woodlands and past the pond. The lower section of the West River Trail is nearly level and ideal for walks. Fort Dummer State Park also offers three easy paths, including the Sunset and Sunrise loop trails.

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

Many trails in the Brattleboro area are dog-friendly, though leash laws typically apply. The extensive Retreat Trails network and the West River Trail are popular choices for walking with dogs. Always check specific park or trail regulations before heading out.

What are some interesting landmarks or points of interest I can see on an easy hike?

You can explore several points of interest. The Madame Sherri Forest, just across the border in New Hampshire, features the dramatic ruins of Madame Sherri's mansion, including a stone staircase. The Retreat Trails within Brattleboro offer an interpretive trail with historical placards. For scenic views, the View of Vermont from Wantastiquet Mountain Stone Post provides sweeping vistas of Brattleboro and the Connecticut River Valley.

Are there any easy trails accessible by public transport?

While many trailheads require a car, the Retreat Trails are located within Brattleboro itself, making them more accessible for those relying on local transport or walking from town. The West River Trail also has accessible sections from Brattleboro.

Where can I find parking for easy hiking trails?

Parking is generally available at the trailheads for most routes. For example, the Black Mountain Trailhead offers parking. Fort Dummer State Park and Sweet Pond State Park also have designated parking areas. For the Madame Sherri Forest, parking is available near the trailhead in Chesterfield, NH.

What is the best time of year to enjoy easy hikes around Brattleboro?

The region's natural beauty is particularly striking during the fall, when the landscape transforms with vibrant autumn colors, making it an excellent time for hiking. Spring offers blooming wildflowers, and summer provides lush greenery. Winter hiking is also possible on many trails, often with opportunities for snowshoeing or Nordic skiing.

Can I spot wildlife on these easy trails?

Yes, the diverse natural areas around Brattleboro offer opportunities for wildlife spotting. Along the West River Trail, you might see ducks, geese, and even bald eagles. The Bonnyvale Environmental Education Center (BEEC) trails are known for their natural habitats, where you can observe various birds and small mammals.

What do other hikers enjoy most about the easy trails in Brattleboro?

The easy trails in Brattleboro are highly rated by the komoot community, with an average score of 5.0 stars from 4 reviews. Hikers often praise the quiet woodlands, well-maintained paths, and the varied scenery, from peaceful ponds to scenic river views.

Are there any easy trails that offer panoramic views?

Yes, some easy trails provide rewarding views. The Black Mountain Loop Trail offers views of the surrounding area. For more expansive vistas, the Hogback Mountain Conservation Area, a short drive from Brattleboro, is famous for its '100-Mile View' across the Green Mountains and into New Hampshire's White Mountains, accessible via easy to moderate trails.

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