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United States
Vermont
Addison County

East Middlebury

The best walks and hikes around East Middlebury

5.0

(7)

97

hikers

23

hikes

Hikes around East Middlebury explore the landscape of the Green Mountain National Forest. The region is characterized by forested hills, river valleys like the one carved by Otter Creek, and a network of well-maintained footpaths. These trails range from gentle riverside walks to more demanding ascents within the Moosalamoo National Recreation Area, offering varied options for hikers.

Best hiking trails around East Middlebury

  • The most popular hiking route is Trail Around Middlebury — Full Loop, a 17.0 mile (27.4…

Last updated: May 16, 2026

#1.

Downtown Middlebury Walk

792m

00:13

10m

10m

Enjoy an easy 0.5-mile walk through downtown Middlebury, featuring views of Otter Creek and the historic Middlebury Falls.

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Easy

13

hikers

6.89km

02:22

350m

350m

Hike the moderate Abbey Pond Trail in Green Mountain National Forest, leading to the serene Abbey Pond and its cascades.

Moderate
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3

hikers

2.51km

00:45

80m

80m

Hike the easy 1.6-mile Chipman Hill Loop in Middlebury, Vermont, offering views of the town, Adirondacks, and Green Mountains.

Easy

1

hikers

27.4km

07:23

350m

350m

Hike the 17.0 miles (27.4 km) Trail Around Middlebury, a difficult loop offering diverse scenery and 1143 feet (348 metres) of elevation gai

Hard

16.0km

04:24

260m

260m

Hike the moderate 10.0-mile Trail Around Middlebury, gaining 845 feet in elevation through diverse landscapes and past Middlebury Falls.

Moderate
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Popular around East Middlebury

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Tips from the Community

Jamie S.
April 25, 2023, Alumni Stadium - Black Panther Statue

Outside of the Middlebury College Alumni Stadium and Youngman Field is a striking sculpture of its mascot: a Panther. Perched on top of a boulder, this large bronze statue is a fun landmark on the south end of the Middlebury campus.

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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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Jamie S.
April 24, 2023, Abbey Pond

Abbey Pond is a beautiful pond in the foothills of Vermont's Green Mountains. This peaceful spot is an excellent place to sip some water, look out for wildlife, and admire the views. This pond is especially stunning in the falls as the changing leaves are reflected in the calm water.

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The Trail Around Middlebury is a unique, 18 mile loop that, as the name indicates, traverses around the entire town of Middlebury, Vermont. This particular segment of trail on the western side of town is also known as the Jackson Trail and is a part of the North Country National Scenic Trail. As you hike alongside a small creek, you get fantastic views of the town of Middlebury and the foothills of the Green Mountains to the east.

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The Pulp Mill Covered Bridge is a historic wooden bridge just north of downtown Middlebury. Also known as the Paper Mill Covered Bridge, this bridge a great example of New England's covered bridges. Built in the mid-19th century, it spans Otter Creek and is a popular spot for photography and sightseeing. Covered bridges are an iconic part of New England's landscape and history. They were once a common sight throughout the region, as they provided a way for travelers to cross rivers and streams in all seasons. While many of the original bridges have been lost to natural disasters and modernization, there are still over 100 covered bridges in Vermont today.

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Middlebury College is a small private liberal arts college and was the first college in the state of Vermont. The main quad on campus is beautiful spot, especially in the fall when the leaves are changing, ringed by historic buildings. Be sure to visit the old chapel on the south end of the quad. Please also be respectul of the students and faculty as you stroll through this picturesque campus.

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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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Jamie S.
April 24, 2023, Main Street

The historic main street of Middlebury offers a quintessential small New England town experience. Unique local shops, art galleries, and restaurants in historic brick buildings line the street. Don't miss the opportunity to admire the beautiful white-steepled church and the picturesque town green.

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Frequently Asked Questions

Are there any easy, family-friendly hikes in the East Middlebury area?

Yes, the region has several gentle trails perfect for families. A great option is the Chipman Hill Loop — Middlebury, a short walk that offers nice views over the town. Another excellent choice is the Robert Frost Interpretive Trail, a one-mile loop that is both easy and educational, featuring poems displayed along the path.

Can I bring my dog on the hiking trails near East Middlebury?

Many trails in the area are dog-friendly, but it's always best to check specific regulations for each trail, especially within the Green Mountain National Forest. Areas like Battell Woods are known to be popular with local dog walkers. Please keep your dog under control and be mindful of other hikers and wildlife.

What's a good hike for panoramic views?

For some of the best views in the region, consider the hike up Snake Mountain. While not directly in East Middlebury, it's a classic local hike that rewards you with stunning panoramic views of Lake Champlain and the Adirondack Mountains from its summit.

Are there any challenging day hikes available?

Absolutely. For a more strenuous outing, the Mount Moosalamoo hike Loop offers a moderately challenging experience within the Moosalamoo National Recreation Area. It provides a solid workout with rewarding vistas and a true sense of being in the Green Mountains.

Where can I find a hike with waterfalls?

The area has some lovely trails that follow waterways. The hike to Abbey Pond is a local favorite, as the trail ascends alongside a brook with numerous small cascades and cataracts. For a more accessible view, Middlebury Falls is located right in town and is a beautiful sight, especially after rainfall.

How long is the full Trail Around Middlebury (TAM)?

The entire Trail Around Middlebury, or TAM, is an 18-mile (approximately 29 km) footpath that encircles the town. It's a significant undertaking to complete in one go, but it has many access points, allowing you to hike shorter sections through forests, fields, and along Otter Creek.

What is the best time of year to hike around East Middlebury?

Hiking is popular from late spring through fall. Summer offers lush green forests, while autumn provides spectacular fall foliage, typically peaking in early to mid-October. Winter is also an option for snowshoeing and cross-country skiing, but be sure to have the proper gear and check trail conditions.

What do other hikers think of the trails in this region?

The trails around East Middlebury are very highly rated by the komoot community. Hikers often praise the variety of terrain, from the peaceful riverside paths along Otter Creek to the more rugged climbs within the Green Mountain National Forest.

Are there any good circular walks or loop trails?

Yes, many trails are designed as loops. Besides the popular loop trails, the Otter Creek Gorge has a well-regarded loop that takes about two hours and offers peaceful, scenic views. It's a great option if you want a contained hike that brings you back to your starting point.

What should I pack for a day hike in the Green Mountains?

For any hike, you should carry water, snacks, a map, and a fully charged phone. Weather can change quickly, so a rain jacket and extra layers are essential. Sturdy hiking shoes are recommended, especially for rocky or muddy trails. For longer hikes, consider a small first-aid kit and insect repellent.

Where can I park for hikes on the Trail Around Middlebury (TAM)?

The TAM has multiple access points with parking. Popular spots include the trailhead for the Otter Creek Gorge, parking near Otter View Park, and various other designated lots where the trail crosses local roads. It's best to consult a TAM map to find the most convenient access point for the section you wish to hike.

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