5.0
(7)
96
hikers
23
hikes
Hiking around East Middlebury offers diverse natural landscapes, characterized by forested hills and river valleys, notably carved by Otter Creek. The region provides an extensive network of easy hiking trails, including sections within the Green Mountain National Forest and the Moosalamoo National Recreation Area. These paths traverse varied terrain, from gentle riverside walks to routes through protected forests.
Last updated: May 18, 2026
3.85km
01:14
270m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
792m
00:13
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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3
hikers
5.43km
01:27
60m
60m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
3
hikers
2.51km
00:45
80m
80m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
3.75km
00:59
30m
30m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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The Trail Around Middlebury traverses around the entire town of Middlebury, Vermont in an 18 mile loop. This particular segment of trail is located within the Battell Woods Natural Area on the southeastern side of town. This generally flat, accessible trail is enjoyable all year round and is a great place to hike in the woods close to town. Be aware, Battle Woods is also quite popular with mountain bikers, so just keep an ear out as you enjoy this section of trail through the old hardwood forest.
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The Means Woods Loop is a pleasant, easy trail in the Means Woods Natural Area. This peaceful loop is especially beautiful in the autumn as the leaves change; this is a great place to be immersed in the classic New England fall peak foliage! As you hike through the woods be careful of roots, which are slippery when wet and are often covered by leaves.
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Middlebury Falls is a unique 20 foot waterfall on Otter Creek right in the center of this picturesque New England town. You get great views of the falls from this spot on a bridge on Main Street. You can also see the ruins of the old Powder House to the lefthand side of the falls. While they are beautiful all year round, Middlebury Falls are particularly interesting in the winter when they partially freeze over.
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Chipman Hill was once the ski hill for Middlebury College, but today is a popular spot for hikers and mountain bikers. The Chipman Hill Top Trail is a strenuous, but enjoyable, trail that takes you around the summit of the hill at its steepest part. Be aware of mountain bikers, who can travel both up and down the Top Trail, as you hike up this popular route.
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This is a peaceful spot to enjoy Otter Creek, which flows down through the center of Middlebury. You can sometimes see wildlife, like birds and insects, along its shores and it is a great place to enjoy the foliage change from green to vibrant hues of orange, yellow, and red in the fall.
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Enjoy views of the Otter Creek Gorge and Belden Falls from the suspension bridge.
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Middlebury Falls is a rather unusual urban waterfall. Take the opportunity to take a tour of the city. Middlebury is one of the most attractive small towns in Vermont, full of shops, art galleries and highly rated restaurants.
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East Middlebury offers 13 easy hiking trails, providing a variety of landscapes from gentle riverside walks to routes through protected forests. These trails are perfect for those looking for a relaxed outdoor experience.
Yes, East Middlebury has several family-friendly options. The Downtown Middlebury Walk is a very short and gentle stroll, perfect for families with young children. For a slightly longer, scenic experience, consider the Trail Around Middlebury: Otter Creek Gorge, which follows the prominent waterway.
Absolutely. The Chipman Hill Loop offers an easy circular path through a popular local spot, once a ski hill. Another great option is the Battell and Means Woods Loop, providing a pleasant walk through forested areas.
The region is characterized by picturesque forested hills and river valleys, notably carved by Otter Creek. You can expect to see diverse natural landscapes, including sections of the Green Mountain National Forest and the Moosalamoo National Recreation Area. The Middlebury Falls, a 20-foot waterfall, is easily accessible from Main Street and can be incorporated into a walk.
While many easy trails offer scenic beauty, for specific views, the Mount Moosalamoo Trail, though featuring some elevation gain, is considered easy and provides rewarding vistas. Additionally, the general topography of forested hills often provides glimpses of the surrounding Vermont landscape.
The area is highly rated by the komoot community, with an average score of 5.0 stars from 7 reviews. Hikers often praise the diverse natural landscapes, the extensive trail networks, and the serene experience of walking through forested hills and river valleys.
Yes, East Middlebury has several points of interest. You can visit the historic Pulp Mill Covered Bridge, which is a beautiful example of local architecture. The Main Street area itself offers a charming stroll, and the Middlebury College Quad is also a notable landmark.
East Middlebury offers beautiful hiking opportunities throughout the year. Spring brings lush greenery, summer provides warm weather for exploration, and autumn showcases spectacular fall foliage. Even winter can be magical for snowshoeing or cross-country skiing on some trails, though conditions should always be checked.
For beginners or those seeking a very short walk, the Downtown Middlebury Walk is an excellent choice, taking only about 12 minutes. The Battell and Means Woods Loop is also relatively short and easy, providing a gentle introduction to the region's trails.
While specific public transport routes directly to trailheads can vary, many trails, particularly sections of the Trail Around Middlebury (TAM), are accessible from the town center of Middlebury. This makes it possible to reach some starting points without a car, especially for walks within or very close to town.
While popular trails like sections of the TAM can see more foot traffic, exploring routes within the Green Mountain National Forest or the Moosalamoo National Recreation Area often provides opportunities for quieter, less crowded experiences, especially during off-peak hours or seasons. The Battell and Means Woods Loop might offer a more tranquil setting.


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