The best walks and hikes around Brattleboro
5.0
(5)
105
hikers
24
hikes
Hiking around Brattleboro offers routes through a landscape shaped by the Connecticut and West Rivers. The region is characterized by conserved forests, rolling hills, and ridgelines with views across the river valley. The trail networks provide a mix of riverside paths and ascents to local peaks.
Best hiking trails around Brattleboro
- The most popular hiking route is the Wantastiquet Mountain Trail — Wantastiquet Mountain Natural Area, a 3.9 mile (6.2 km) trail that takes about 2 hours 30 minutes to complete. This moderate hike involves an ascent of Wantastiquet Mountain, located just across the river in New Hampshire.
- Another top favourite among local hiking enthusiasts is the Black Mountain loop — Black Mountain Natural Area, an easy 3.2 mile (5.2 km) path. The route leads through the Black Mountain Natural Area with some steady inclines.
- Local hiking enthusiasts also love the Daniels Mountain & Ann Stokes loop — Madame Sherri Forest, a 4.0 mile (6.4 km) trail leading through Madame Sherri Forest, often completed in about 1 hour 55 minutes.
- Hiking around Brattleboro is defined by its extensive trail networks, forested hills, and riverside paths. The collection of routes includes options for different ability levels, from gentle walks to more challenging ascents.
- The routes in Brattleboro are highly rated by the komoot community with an average score of 5.0 stars from a number of reviews. More than 100 hikers have used komoot to explore Brattleboro's varied terrain.
Last updated: May 9, 2026
7
hikers
3.37km
01:03
120m
120m
Embark on the Anne Stokes Loop Trail for an easy hike through the serene Madame Sherri Forest. This route spans 2.1 miles (3.4 km) and involves a gentle elevation gain of 398 feet (121 metres), making it suitable for most hikers. You can expect to complete the loop in about 1 hour and 2 minutes, enjoying the peaceful hemlock forests and the tranquil Indian Pond, which is framed by open ledges. The trail offers a pleasant outdoor experience with a mix of natural beauty and historical intrigue.
When planning your visit, note that the trail is part of the Madame Sherri Forest, and the Madame Sherri House ruins are conveniently located a short walk from the parking area. While the route is rated as easy, some sections can be rocky and steep, especially after rain, so be sure to wear appropriate footwear for your comfort and safety. The trail is particularly beautiful during the fall foliage season, offering vibrant colors.
The Anne Stokes Loop Trail is notable for its connection to the Madame Sherri House ruins, where you can explore old foundations and a grand stone staircase, adding a historical dimension to your outdoor adventure. As you hike, keep an eye out for local wildlife, including beavers near the pond. This trail provides a unique blend of natural scenery and historical points of interest within the region.
2
hikers
2.45km
00:46
90m
90m
Embark on a moderate hike along the Ann Stokes Trail to Indian Pond, a refreshing 1.5-mile (2.4 km) route that takes about 45 minutes to complete. You will gain 287 feet (87 metres) in elevation as you wander through dense deciduous woodland and peaceful hemlock forests. The trail culminates at Indian Pond, a secluded mountain lake beautifully framed by open ledges and the talus slopes of Mine Ledge, offering a serene natural escape.
Planning your visit is straightforward, as the Madame Sherri Forest provides accessible parking right near the trailhead. This makes starting your adventure convenient, whether you are heading out for a quick morning walk or an afternoon exploration. The trail is generally well-maintained, making it suitable for most hikers looking for a pleasant outdoor experience without extensive preparation.
Beyond the natural beauty of the pond and forests, the area holds a unique historical charm. You can easily extend your trip with a short side trail to visit the intriguing ruins of Madame Sherri's
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2.93km
01:09
210m
20m
Hike the moderate 1.8-mile Mine Ledge Trail in Wantastiquet Mountain Natural Area for panoramic views and historical ruins.
2.91km
00:45
20m
10m
Hike the easy 1.8-mile West River Trail - Lower Section in Riverstone Preserve, offering riverside views and historic railroad remnants.
739m
00:15
10m
10m
Hike the moderate Mine Ledge Trail for 0.5 miles (0.7 km) to enjoy panoramic views and diverse forest terrain in 14 minutes.
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Other adventures around Brattleboro
Tips from the Community
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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You can see to Indian Pond and across the trees toward Madame Sherri Forest and Daniels Mountain. The views are wonderful.
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A ledge of triangular rocks just out into the sky on the crest of the mountain. The views from here are stunning, especially in autumn.
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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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It's a nice challenge for any hiker with a rewarding view at the end.
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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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This summit is the greatest highlight of this hike. It offers views of Brattleboro, the Green Mountains, and the West River.
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Frequently Asked Questions
Are there any easy hikes suitable for families in the Brattleboro area?
Yes, the region has several family-friendly options. For a gentle walk with minimal elevation, consider the River Trail — Wantastiquet Mountain Natural Area. It's a relatively flat path that follows the river, making it ideal for hikers of all ages.
Can I bring my dog on the hiking trails?
Many trails in and around Brattleboro are dog-friendly, but policies can vary. It's common practice to keep dogs on a leash, especially in popular areas like state parks and natural areas, to protect wildlife and ensure a good experience for all hikers. Always check the specific regulations for the trail you plan to visit before you go.
Which hike offers great views of the river valley?
For expansive views, the hike to the summit of Hogback Mountain is a local favorite. The conservation area provides panoramic vistas of the surrounding landscape, which are especially stunning during the fall foliage season. The trails there are well-regarded and offer a rewarding experience.
Are there any challenging hikes for more experienced hikers?
Yes, if you're looking for a more strenuous outing, the Wantastiquet Mountain & Monadnock Trails Loop – Madame Sherri Forest offers a difficult-rated challenge. This route involves more significant elevation gain and rugged terrain compared to other trails in the immediate area.
What are the trail conditions like in Madame Sherri Forest?
The trails in Madame Sherri Forest, such as the Daniels Mountain & Ann Stokes loop, are generally well-maintained but feature natural, varied terrain. You can expect a mix of forest paths with some rocky sections and moderate inclines. It's a popular spot known for its lush scenery and the ruins of Madame Sherri's castle.
What kind of terrain can I expect on the Retreat Trails?
The Retreat Trails feature a network of historic carriage roads and footpaths through conserved forests. The terrain is generally gentle with some rolling hills, making it suitable for walking and easy hiking. The paths are well-defined, and you can also find the Woodlands Interpretive Trail, which has placards about the area's natural history.
Are there any good circular hikes available?
Yes, many routes in the area are loops, allowing you to enjoy a varied hike without retracing your steps. A great example is the Black Mountain loop — Black Mountain Natural Area, which takes you through a beautiful forest on a well-marked path with some steady but manageable climbs.
What are some popular places for hiking around Brattleboro?
Hikers have several highly-regarded options in the area. Key spots include:
- Wantastiquet Mountain Natural Area: A very popular destination just across the river, offering trails with rewarding summit views.
- Fort Dummer State Park: Known for its well-maintained, easy trails through the forest, making it a local favorite for accessible hiking and camping.
- Hogback Mountain Conservation Area: Famous for its incredible panoramic views that are easily accessible.
- Black Mountain Natural Area: A great choice for a moderate hike with some steep sections through a quiet, well-preserved forest.
What do other hikers enjoy most about the trails in Brattleboro?
The area is highly rated by the komoot community, with an average score of 5.0 stars. Hikers often praise the variety of trails, from peaceful riverside walks to more challenging ascents with rewarding views. The well-preserved forests and the scenic beauty of the Connecticut River Valley are frequently mentioned as highlights.
What should I wear for a hike in Vermont?
Layering is key. Wear moisture-wicking clothing to stay dry and comfortable. A waterproof or windproof outer layer is essential, as weather can change quickly. Sturdy hiking shoes or boots with good grip are a must for the region's varied terrain. In cooler months, add a hat and gloves.
Is it possible to go hiking in the winter?
Yes, winter hiking is a popular activity around Brattleboro, but it requires preparation. Trails can be icy and covered in snow. You'll need appropriate gear like microspikes or snowshoes for traction, as well as warm, waterproof layers. Always check trail conditions and weather forecasts before heading out.
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