4.5
(2)
135
hikers
21
hikes
Hiking around Middlebury offers diverse landscapes, from the gentle paths along Otter Creek to the forested hillsides surrounding the town. The region is characterized by its position between the Green Mountains to the east and the Champlain Valley to the west, providing a mix of open fields, woodlands, and riverine environments. Local features like Chipman Hill and sections of the Trail Around Middlebury (TAM) contribute to a varied hiking experience. This area provides accessible trails suitable for easy excursions.
Last updated: June 24, 2026
792m
00:13
10m
10m
Discover the charm of Middlebury, Vermont, on the Downtown Middlebury Walk, an easy 0.5-mile (0.8 km) route that takes just 12 minutes to complete. This accessible trail offers a delightful…
4.0
(1)
9
hikers
3.95km
01:05
60m
60m
Hike the easy 2.5-mile Otter Creek Gorge Trail, featuring suspension bridges, a waterfall, and diverse forest ecosystems.

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4
hikers
5.43km
01:27
60m
60m
Hike the easy 3.4-mile Trail Around Middlebury: Otter Creek Gorge loop, featuring stunning gorge views and a hidden waterfall.
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.
3.75km
00:59
30m
30m
This easy 2.3-mile hike through Battell and Means Woods in Middlebury, Vermont, offers a peaceful loop through old hardwood forests.
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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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Middlebury offers a great selection of easy hiking trails, with 12 routes specifically categorized as easy. In total, there are 18 hiking routes in the area, providing diverse options for all skill levels.
Yes, many easy trails in Middlebury are suitable for families. The Otter Creek Gorge Trail is a popular choice, offering scenic views along the creek. The Trail Around Middlebury: Otter Creek Gorge section is also excellent for a family outing, providing a gentle path through varied landscapes.
You can discover several natural highlights on easy hikes. The Otter Creek Gorge Trail offers views of the impressive gorge. You can also visit the Middlebury Falls, a unique 20-foot waterfall right in the town center, which is easily accessible from the Downtown Middlebury Walk. Additionally, Red Rock Pond is a beautiful spot to explore.
Absolutely. The Chipman Hill Loop is a fantastic easy loop trail that takes you through local woodlands and up Chipman Hill, offering convenient access within town. Another great option is the Battell and Means Woods Loop, which provides a pleasant circuit through forested areas.
The easy trails in Middlebury are highly regarded by the komoot community, with an average rating of 4.7 stars. Hikers frequently praise the well-maintained paths, the accessibility of trails like the Trail Around Middlebury (TAM), and the scenic beauty of Otter Creek and the surrounding woodlands.
Many easy trails in Middlebury, particularly sections of the Trail Around Middlebury (TAM) and trails within the Green Mountain National Forest, are dog-friendly. Always ensure your dog is on a leash and check specific trail regulations before heading out.
The best time for easy hikes in Middlebury is generally from spring through fall. Spring offers lush greenery, while summer provides warm weather for exploring. Fall is particularly stunning with vibrant foliage. Even winter can be beautiful for snowshoeing or cross-country skiing on some trails, though conditions require appropriate gear.
While Middlebury itself has some local public transport options, many trailheads, especially those further out in the Green Mountain National Forest, are best accessed by car. However, trails like the Downtown Middlebury Walk and sections of the Trail Around Middlebury (TAM) are easily reachable on foot from the town center.
The duration of easy hikes varies. Shorter routes like the Downtown Middlebury Walk can be completed in about 12 minutes. Longer easy trails, such as the Otter Creek Gorge Trail, might take around an hour, while the Chipman Hill Loop typically takes about 45 minutes.
Yes, many easy trails around Middlebury offer convenient parking. Trails close to the town center, like those accessing Chipman Hill or sections of the TAM, often have nearby public parking. For trails further afield, such as those in the Moosalamoo National Recreation Area or Branbury State Park, designated parking lots are usually available at trailheads.
While many easy trails focus on local woodlands and riverbanks, for broader scenic views, consider trails that ascend gently, like the Chipman Hill Loop which offers glimpses over the town. For truly expansive vistas, Snake Mountain, though a bit more of a gradual ascent, provides breathtaking panoramic views of the Champlain Valley and Adirondacks, and has accessible trails.
The Downtown Middlebury Walk is perfect for this, as it takes you directly through the town center where you'll find numerous cafes, restaurants, and shops. Sections of the Trail Around Middlebury (TAM) that pass close to the village also offer easy access to amenities.


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