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Routes
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United States
Vermont
Addison County

East Middlebury

Easy hikes and walks around East Middlebury

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.

Best easy hiking trails around East Middlebury

  • The most popular easy hiking route is Mount Moosalamoo Trail, a 2.4 miles (3.9…

Last updated: May 18, 2026

#1.

Mount Moosalamoo Trail

3.85km

01:14

270m

20m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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3

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

3

hikers

2.51km

00:45

80m

80m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Tips from the Community

Jamie S.
April 24, 2023, Trail Around Middlebury (Battell Woods Section)

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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Jamie S.
April 24, 2023, Means Woods Loop

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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Jamie S.
April 24, 2023, Middlebury Falls

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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Jamie S.
April 24, 2023, Otter Creek

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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Frequently Asked Questions

How many easy hiking trails can I find around East Middlebury?

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.

Are there family-friendly easy hikes in East Middlebury?

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.

Are there any easy circular routes for hiking in East Middlebury?

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.

What kind of natural features can I expect to see on easy hikes in East Middlebury?

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.

Are there any easy trails with good views in East Middlebury?

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.

What do other hikers enjoy most about hiking in East Middlebury?

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.

Are there any historical or interesting landmarks near the easy hiking trails?

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.

What is the best time of year for easy hikes in East Middlebury?

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.

Are there any short, easy hikes suitable for beginners?

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.

Can I access easy hiking trails in East Middlebury using public transport?

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.

Are there any less crowded easy hikes in East Middlebury?

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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