5.0
(2)
25
hikers
4
hikes
Hiking around Bennington, Vermont, is characterized by its location between the Green Mountains and the Taconic Range, offering diverse terrain. The region features dense forests, rolling hills, and varied elevations, providing a range of hiking experiences. Trails often traverse woodlands, follow rivers, and lead to open viewpoints. This landscape provides opportunities for both gentle strolls and more challenging ascents.
Last updated: May 16, 2026
5
hikers
2.32km
00:47
110m
110m
The Hedgehog Ridge Trail offers an easy hiking experience, covering 1.4 miles (2.3 km) with a gentle elevation gain of 377 feet (115 metres). You can expect to complete this…
5.0
(1)
4
hikers
6.33km
02:07
300m
300m
Embark on the Shannon's, Summit West and Lower Link Trail for a moderate hike through varied terrain in Crotched Mountain Town Forest. This route spans 3.9 miles (6.3 km) and…

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3
hikers
5.54km
01:29
60m
60m
Embark on the Summit East and Summit West Loop Trail for an easy hike through the varied ecosystems of Crotched Mountain Town Forest. This pleasant route spans 3.4 miles (5.5…
4
hikers
5.99km
01:45
150m
150m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
4
hikers
6.94km
02:18
320m
320m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Popular around Bennington
Great view from the top of Crotched Mountain. During your run to the top, you will pass other view points into the valley, but the peak is definitely worth the effort as it gives you the best view in the area.
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This is a preserved area composed of swamps, streams, grassland, vernal pools and ledges, and is home to diverse fauna including: wild turkey, moose, whitetail deer, hawks, barred owl, snowshoe hare, beaver, mink; and many other wild animals. Being the biggest town forest preserved by Fracestown, it extends from Farrington Road and Route 136 on the south side of Crotched Mt. to East Road.
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Crotched Mountain offers many hiking trails from different slopes, traversing scenic viewpoints sitting in the “crotches” around the mountain, offering views of the woodland and cities around. At the summit, there is a cell tower which is not accessible by the trails. Here the first wind farm in the world was built in 1980, but the company went out of service and the 20 turbines were dismantled years ago. Crotched Mountain is also a popular ski station in New Hampshire.
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Bennington, nestled between the Green Mountains and the Taconic Range, offers a diverse range of hiking experiences. You'll find trails traversing dense forests, rolling hills, and river valleys. Options range from gentle woodland strolls to more challenging ascents with rewarding views, including sections of the iconic Appalachian Trail and Long Trail.
Yes, Bennington has several easy trails perfect for beginners or families. The Summit East and Summit West Loop Trail is an easy 5.5 km path. Another great option is the Bald Mountain loop from Willard Pond, which is 4.3 km and also rated easy. The Mile-Around-Woods Loop in North Bennington is also known as a family-friendly 2.2-mile walk through quiet woodlands.
Many trails in Bennington lead to open summits or lookouts with expansive vistas. Bald Mountain is a popular choice, offering panoramic 360-degree views from its summit, with a notable spur trail to White Rocks providing excellent views of Bennington. Harmon Hill via the Appalachian Trail also leads to an open summit with views over the town and surrounding ranges. The Bennington Area Trail System (BATS) includes trails like Zaphod's Run, which leads to a scenic lookout over Bennington and Mount Anthony.
Yes, Bennington features several loop trails. The Summit East and Summit West Loop Trail is an easy 5.5 km loop. For a slightly longer option, consider the Skatutakee Mountain – Thumb Mountain loop from Skatutakee Mountain, a moderate 7.0 km trail. The Bald Mountain loop from Willard Pond is another easy 4.3 km loop. The Mile-Around-Woods Loop is also a well-known 2.2-mile loop.
Bennington offers great hiking opportunities throughout much of the year. Spring brings lush greenery, while summer provides shaded paths through forests. However, the fall foliage season is particularly stunning, with numerous trails leading to open viewpoints that showcase the vibrant autumn colors of the Green and Taconic Mountains. Winter hiking is also possible, though trails may require appropriate gear.
Many trails in the Bennington area are dog-friendly, but it's always best to check specific trail regulations before heading out. Generally, dogs are welcome on leash in most state parks and forest trails. For example, the Mile-Around-Woods Loop is a popular spot for dog walkers.
While hiking in Bennington, you can encounter diverse natural features. The region is rich in forested trails, offering opportunities to observe local flora and fauna. Rivers like the Walloomsac and picturesque bodies of water such as Little Pond and Lake Paran add to the scenic beauty. Some trails, like the Robert Frost Trail, even meander through an orchard and red pine strand planted by Frost himself, offering a blend of nature and literary history.
Parking availability varies by trailhead. Many popular trails, especially those within state parks or designated trail systems like the Bennington Area Trail System (BATS), have dedicated parking lots. For trails like Harmon Hill via the Appalachian Trail, there are often specific parking areas for hikers. It's advisable to check the starting point details for your chosen route for precise parking information.
The hiking routes in Bennington are highly rated by the komoot community, with an average score of 5.0 stars from over 4 reviews. Hikers often praise the varied terrain, from dense woodlands to open viewpoints, and the well-maintained paths that cater to different ability levels. Over 40 hikers have used komoot to explore Bennington's diverse landscape.
Yes, several trails in Bennington incorporate water features. Greenberg Headwaters Park, within walking distance of downtown, features trails that run alongside the Walloomsac River, offering excellent spots for wildlife observation. The Robert Frost Trail also meanders along waterways, connecting Lake Paran to the Robert Frost Stone House Museum.
Hike durations in Bennington vary depending on the trail's length and difficulty. Easy trails like the Summit East and Summit West Loop Trail (5.5 km) can be completed in about 1 hour 29 minutes. Moderate routes, such as Shannon's, Summit West and Lower Link Trail (6.3 km), typically take around 2 hours 7 minutes. Longer moderate trails like the Crotched Mountain loop from Fleck Conservation Area (6.9 km) might take closer to 2 hours 18 minutes.


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