4.8
(56)
860
hikers
38
hikes
Hikes in Windham County explore the southeastern corner of Vermont, an area characterized by the rolling hills of the Green Mountains, dense forests, and numerous lakes and ponds. The terrain offers a mix of gentle lakeside paths and more demanding ascents to mountain summits. Many trails, including sections of the Appalachian Trail, wind through state parks and national forests.
Last updated: April 26, 2026
5.0
(1)
16
hikers
17.6km
05:25
610m
600m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
16
hikers
3.31km
00:59
0m
280m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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5.0
(1)
11
hikers
5.63km
01:38
160m
120m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
9
hikers
5.60km
01:59
510m
0m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
3
hikers
3.91km
01:09
100m
100m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
3.48km
01:07
170m
100m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
4.34km
01:13
100m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.37km
01:43
530m
0m
Moderate hike. Good fitness required. 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.
993m
00:18
50m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Stratton Mountain is one of the most iconic peaks on the Long Trail, but not for its height, but rather for its historical significance. It was here in 1909 that James P. Taylor first imagined a “footpath in the wilderness,” which eventually became the Long Trail. The summit is forested, but a restored fire tower (that you can climb!) offers expansive 360-degree views of southern Vermont and the surrounding peaks. Today, Stratton is also home to a major ski resort, but the Long Trail bypasses the commercial slopes, staying on a quieter, wooded path. A nearby shelter, Stratton Pond Shelter, provides a peaceful overnight spot, just a short hike from the summit. This is a pretty built-up shelter (especially in comparison to the more common, simple three-sided lean-tos) so it's worth checking out even if you're not spending the night.
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The top of Stratton Mountain supports a fire lookout tower that is on the National Register of Historic Places. As you might imagine, the views from up here are great.
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From the top of this mountain you are close to the ski resort "L'Ermitage". You also have exceptional views, especially on the Harriman Reservoir.
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This is a wonderful and very picturesque spot. In summer you can enjoy the pool under the waterfall with fresh water ideal for cooling off after the walk. Remember that it is not allowed to climb the waterfall and the surface of the stones is really slippery
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It is worth reaching the top of the dam. The road in itself is a real pass. When you reach the top the views are amazing, until you get to see Straton Ski Resort
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Yes, the area offers several great options for families. The Grout Pond Loop is a gentle walk around a scenic pond in the Green Mountain National Forest. Another excellent choice is the Hoot Toot & Whistle Trail in Wilmington, which is a relatively flat path suitable for all ages.
Many trails in Windham County are dog-friendly, but policies can vary, especially in state parks and on private land. Trails within the Green Mountain National Forest are generally welcoming to leashed dogs. Always check specific regulations for the trail you plan to hike and be prepared to keep your dog on a leash.
If you prefer to end your hike where you started, there are several loop trails available. The Black Mountain loop offers a satisfying circuit with some elevation gain through the Black Mountain Natural Area. For a more challenging day out, the Stratton Mountain, Stratton Pond and Bourne Pond loop is a long and rewarding trek for experienced hikers.
Yes, Windham County is home to significant sections of famous long-distance paths. The Appalachian Trail runs through the area, offering challenging climbs like the ascent to Stratton Mountain. You can also explore parts of the West River Trail near Brattleboro for an extended walk.
The trails in this region are highly regarded by the komoot community, with an average rating of 4.8 out of 5 stars. Hikers often praise the beautiful forests of the Green Mountains, the well-maintained paths, and the variety of trails that range from peaceful lakeside walks to challenging mountain summits.
There are over 30 curated hiking routes in Windham County on komoot. The network includes a mix of easy, moderate, and difficult trails, ensuring options for every skill level, from short family walks to strenuous all-day treks.
Definitely. For a rewarding view without a major climb, the fire tower on the Mount Olga loop provides a fantastic panorama. For a more expansive vista, the summit of Stratton Mountain offers one of the best viewpoints in southern Vermont.
Summer and fall are the most popular seasons for hiking. Summer offers lush green forests and pleasant weather, while autumn brings spectacular fall foliage, typically peaking in early to mid-October. Spring can be wet and muddy, and winter hiking is possible with proper gear like snowshoes or microspikes, but be prepared for cold and snowy conditions.
Yes, the Putney Mountain area has some great trails. The Dino & Hilton Trail is a moderate route that explores the woodlands and offers a peaceful hiking experience away from the larger peaks.
Absolutely. State parks are excellent destinations for hiking in the region. Lowell Lake State Park features a beautiful and easy trail around the lake, while Molly Stark State Park is home to the popular Mount Olga trail.
For any hike, you should bring water, snacks, a map, and a fully charged phone. Sturdy hiking shoes are recommended as trails can be rocky and uneven.
The weather in the Green Mountains can change quickly, so it's wise to pack layers, including a waterproof jacket, even on a sunny day. For longer hikes, a first-aid kit and headlamp are also essential.
Yes, several trails feature beautiful bodies of water. The hike to Stratton Pond is a classic moderate outing that leads to one of the largest and most scenic ponds along the Appalachian Trail in Vermont. It's a great destination for a day hike.


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