4.5
(15)
121
hikers
26
hikes
Hikes in Glastenbury Wilderness explore a remote section of the Green Mountain National Forest northeast of Bennington, Vermont. The region's landscape is defined by a prominent ridgeline, dense forests of fir and spruce, and hilly terrain. The trail network includes sections of the Appalachian Trail and Long Trail, offering routes that range from short walks to challenging multi-day hikes.
Last updated: April 30, 2026
8
hikers
13.6km
04:17
620m
260m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
3.50km
01:17
310m
10m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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1.47km
00:29
120m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
10
hikers
6.58km
02:27
460m
460m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
3.52km
01:23
400m
0m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Popular around Glastenbury Wilderness
Right next to VT-9 on the Long/ Appalachian Trail is a small stream with wooden foot bridge. This is a nice place to fill water bottles and snap a few photos before continuing onward on the Long/ Appalachian Trail toward the Melville-Nauheim Shelter and Glastenbury Mountain or crossing the road toward the scenic Harmon Hill.
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Maple Hill stands at 2,690 feet and is situated on the Long/ Appalachian Trails. This scenic spot is a great destination for a day hike from the Bennington-Woodford area. You get lovely views from the top of the hill where is it clearcut for some power lines. Maple Hill is a great spot to rest, drink some water, and take some photos before continuing onward.
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The Melville-Nauheim Shelter is shelter along the Appalachian/ Long Trail. Like most shelters in this area there is a lean-to (a three-sided, covered structure), places to pitch tents or tarps, pit-toilets, and a water source. Even if you are just day hiking, Melville-Nauheim Shelter might be a nice place to stop, use the bathroom, and get a feeling for what it might be like to thru-hike on these famous trails.
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Bald Mountain sits at 2,857 feet and is a popular summit in large part due its accessibility from the town of Bennington and scenic position. The name Bald Mountain likely comes from when a forest fire in the early 20th century burned the most of the vegetation on the summit. Although the trees have regrown since then, and obscure some of the views, you can still see through them to east and south from the top of this lovely peak in the Green Mountains.
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The Bear Wallow Trail ascends the east side of Bald Mountain for about two miles with a little over 1,500 feet of elevation. In comparison to the more popular Bald Mountain Trail, the Bear Wallow Trail offers a shorter, but still quite pleasant way, to summit Bald Mountain. Following blue blazes up an old road through the dense forest, you eventually reach the Forest Service Boundary (marked with a red blaze) at about 0.5 miles. From there the trail narrows and climbs steadily for about 1.5 miles until you reach the Bald Mountain Trail. From there you can continue on to the summit of Bald Mountain.
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The top of Harmon Hill is covered by huge green ferns and dotted with trees, which stands in stark contrast to the rest of the area which is densely forested. This is because the summit of Harmon Hill is kept clear by controlled burns that allow for fantastic views of the town of Bennington and the surrounding area. This lush meadow is a perfect place to rest, admire the views, and sip some water before continuing on your hike.
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Yes, dogs are generally permitted in the Glastenbury Wilderness, but they must be under your control at all times. Given the remote nature of the area and the presence of wildlife like black bears, it's recommended to keep your dog on a leash for their safety and the protection of the local ecosystem. Always pack out any waste.
The trails in Glastenbury Wilderness are characterized by their remote, backcountry feel. You can expect hilly terrain with several summits over 2,000 feet. The paths wind through dense forests of balsam fir, red spruce, and birch, with a thick undergrowth of ferns and berries. Trails can be rocky and rooted, and some sections, particularly on the way to the higher peaks, involve steep and strenuous climbs.
While many trails are challenging, there are easier options. The region offers several less strenuous paths, such as the relatively flat Little Pond Trail, which is a great choice for a more leisurely outing. For a short but rewarding climb with good views, consider the Maple Hill via the Appalachian Trail, a moderate walk through pleasant woodland.
Parking is available at designated trailheads, but lots can be small and fill up quickly, especially on weekends. The main access points for the Appalachian/Long Trail, such as near Route 9 for Harmon Hill, have established parking areas. It's always a good idea to arrive early to secure a spot and to not park on the road where it could obstruct traffic.
Yes, backpacking is a popular way to experience the area. The Long Trail/Appalachian Trail has several shelters, such as the Goddard Shelter near a pond, which are available for thru-hikers and backpackers. Dispersed camping is also permitted, but you must follow Leave No Trace principles and camp at least 200 feet from trails and water sources. Be sure to check the Green Mountain National Forest regulations before your trip.
Winter transforms the wilderness into a quiet, snowy landscape. The trails become suitable for snowshoeing and experienced cross-country skiers. However, conditions can be harsh and demanding. Trails are not groomed, and deep snow, ice, and cold temperatures are standard. Proper winter gear, including traction devices like microspikes or crampons, is essential for safety.
The most famous viewpoint is from the historic fire tower atop Glastenbury Mountain. It's one of the few in Vermont that hikers can still climb, offering spectacular panoramic views of the surrounding Green Mountains. The summit of Bald Mountain also provides rewarding vistas of the area.
There are over 15 marked trails available for hiking. The network includes the famous Long Trail/Appalachian Trail which runs the length of the wilderness, as well as numerous side trails leading to peaks and ponds. This provides a wide variety of options, from short walks to multi-day backpacking adventures.
The area is well-regarded by the komoot community, with an average rating of 4.3 stars. Hikers often praise the remote, wild feeling of the trails and the beautiful, dense forests. The challenging but rewarding climbs to peaks like Glastenbury Mountain are frequently mentioned as highlights.
Yes, you can create a challenging backpacking loop by combining different trails. A popular option is to hike a section of the Long Trail and connect with the West Ridge Trail to create a loop over Glastenbury Mountain. This is a strenuous, multi-day trek that requires careful planning and navigation skills.
The 'Bennington Triangle' is a term coined by an author to describe an area centered on Glastenbury Mountain where several people went missing between the 1940s and 1950s. While it adds a layer of local folklore to the region, it doesn't impact the current hiking experience. The trails are well-marked, but the stories serve as a reminder of the wilderness's remote and rugged nature.


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