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.
Last updated: June 23, 2026
7
hikers
3.37km
01:03
120m
120m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
2.91km
00:45
20m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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993m
00:18
50m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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.
10
hikers
4.85km
01:18
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Popular around Brattleboro
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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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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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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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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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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There are 11 easy hiking trails around Brattleboro, offering diverse options for exploring the region's natural beauty.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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