Best attractions and places to see around East Middlebury include a blend of historical landmarks, natural features, and cultural sites. This charming census-designated place in Vermont offers visitors opportunities to explore its rich past and scenic landscapes. The area is characterized by its river gorges, historic bridges, and proximity to the Green Mountains, providing a variety of outdoor and cultural experiences.
Last updated: May 16, 2026
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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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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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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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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 is rich in history. You can visit the historic Waybury Inn, famous for its appearance in the TV series *Newhart* and a frequent haunt of Robert Frost. Another notable site is the Pulp Mill Covered Bridge, a mid-19th-century wooden bridge spanning Otter Creek, perfect for photography. The Community House and Sarah Partridge Library also house local historical artifacts, and you can find the ruins of the East Middlebury Iron Works along the Middlebury River.
Absolutely! The Middlebury Falls, a unique 20-foot waterfall on Otter Creek, offers great views from Main Street. The East Middlebury Gorge, carved by the Middlebury River, provides stunning natural beauty and opportunities for wildlife observation. The Middlebury River itself is a significant natural feature, and the area is close to the Green Mountain National Forest, offering extensive outdoor recreation.
The East Middlebury area is excellent for outdoor enthusiasts. You can explore various hiking trails, including segments of the Trail Around Middlebury, an 18-mile loop encircling the town. For more options, check out guides for hiking around East Middlebury or easy hikes. There are also opportunities for gravel biking with routes like the Middlebury Falls – Pulp Mill Covered Bridge loop.
Yes, many attractions in East Middlebury are suitable for families. The Middlebury Falls and the Pulp Mill Covered Bridge are popular spots for all ages. The Trail Around Middlebury offers accessible hiking and biking for various skill levels, making it a great family activity. Strolling through Main Street in Middlebury also provides a pleasant experience with local shops and a picturesque town green.
East Middlebury is beautiful year-round, but the best time depends on your interests. Autumn is particularly stunning when the leaves change, making the Middlebury College Quad and surrounding areas vibrant. Warmer months are ideal for swimming in the East Middlebury Gorge and enjoying outdoor activities. Winter offers a unique perspective, especially when the Middlebury Falls partially freeze over.
To experience local culture, visit Main Street in Middlebury, which offers a quintessential small New England town experience with unique shops, art galleries, and restaurants. The Middlebury College Quad is also a beautiful cultural spot. The Henry Sheldon Museum of Vermont History in Middlebury provides insights into the region's past, and the East Middlebury Historical Society, located in the Sarah Partridge Community House, offers a deeper dive into local history.
The Main Street area of Middlebury is generally accessible, offering a pleasant experience with shops and restaurants. While specific wheelchair-accessible trails are not extensively detailed, the Trail Around Middlebury (TAM) is known for linking conserved properties and local landmarks, offering accessible sections for various skill levels. It's always recommended to check specific trail conditions for the most up-to-date accessibility information.
Visitors frequently appreciate the blend of historical charm and natural beauty. The unique Middlebury Falls and the picturesque Pulp Mill Covered Bridge are often highlighted for their scenic appeal. Many also enjoy the quaint atmosphere of Main Street and the serene beauty of the Middlebury College Quad, especially during the fall foliage season.
The historic Waybury Inn is a prominent accommodation option in East Middlebury, known for its charm and history. For dining and additional accommodation, Main Street in Middlebury offers a variety of local shops, art galleries, and highly-rated restaurants in historic brick buildings.
Yes, there are several easy hiking options. The Trail Around Middlebury (TAM) offers accessible sections suitable for beginners. You can find more easy routes in the Easy hikes around East Middlebury guide, which includes trails like the Downtown Middlebury Walk and the Chipman Hill Loop.
For Middlebury Falls, parking is generally available in the downtown Middlebury area, as the falls are centrally located and visible from Main Street. For the Pulp Mill Covered Bridge, there are usually designated parking spots nearby, as it's a popular photography and sightseeing location just north of downtown Middlebury.


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