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Routes
Gravel rides
United States
Vermont
Addison County

Middlebury

The best gravel rides around Middlebury

3.3

(4)

34

riders

7

rides

Gravel biking around Middlebury, Vermont, offers diverse terrain within the Champlain Valley and near the Green Mountain National Forest. The region features extensive networks of unpaved roads and rolling hills, providing varied surfaces for gravel cyclists. These routes often traverse agricultural landscapes and offer views of distant mountains. The area is characterized by a mix of forested sections and open farmlands, with elevations ranging from valley floors to challenging climbs.

Best gravel bike trails around Middlebury

  • The most popular gravel…

Last updated: April 30, 2026

4

riders

#1.

Middlebury Falls – Middlebury College Quad loop from Middlebury

49.8km

03:04

710m

710m

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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3.0

(1)

4

riders

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

4

riders

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Popular around Middlebury

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Tips from the Community

Jamie S.
June 25, 2025, 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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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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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 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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This black panther statue is located near the Alumni Stadium in Middlebury. It is necessary to look for it, because it is located on a height.

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Frequently Asked Questions

How many gravel bike trails are there in Middlebury?

Middlebury offers a network of over 10 gravel bike trails, catering to various skill levels. These routes traverse the scenic Champlain Valley and venture near the Green Mountain National Forest, providing diverse riding experiences.

What kind of terrain can I expect on Middlebury's gravel bike trails?

You can expect a mix of terrain, from the rolling hills and agricultural landscapes of the Champlain Valley to more challenging sections near the Green Mountain National Forest. Many routes feature extensive unpaved roads, with some offering significant elevation gains. The region is known for its diverse surfaces, making it ideal for gravel biking.

Are there challenging gravel routes in Middlebury?

Yes, Middlebury has several challenging gravel routes. For instance, the Middlebury Falls – Middlebury College Quad loop from Middlebury is a difficult 31-mile trail with substantial elevation gain. Another demanding option is the Willmarth Woods loop from Middlebury, which explores forested areas over nearly 30 miles with significant climbs.

Are there any easy or family-friendly gravel bike trails in Middlebury?

While many routes offer moderate challenges, some sections of the Trail Around Middlebury (TAM) are suitable for easier rides, offering an accessible way to experience local scenery. For a moderate gravel experience, consider the Middlebury Falls – Pulp Mill Covered Bridge loop from Middlebury, which is about 18.5 miles long and leads through picturesque local landscapes.

What can I see along the gravel bike trails in Middlebury?

Many gravel routes in Middlebury offer scenic views and pass by notable landmarks. You might encounter natural features like the Middlebury Falls or the historic Pulp Mill Covered Bridge. Some trails also lead through charming areas like Main Street or past the Middlebury College Quad, offering a blend of natural beauty and local culture.

Are there any circular gravel bike routes around Middlebury?

Yes, many of Middlebury's gravel bike routes are designed as loops, allowing you to start and finish in the same location. Examples include the Middlebury Falls – Middlebury College Quad loop from Middlebury and the Main Street – Middlebury Falls loop from Middlebury, providing convenient round trips.

What do other gravel bikers enjoy the most about gravel biking in Middlebury?

The gravel biking experience in Middlebury is highly rated by the komoot community, with an average score of 3.0 stars. Riders often praise the diverse terrain, the extensive network of unpaved roads, and the scenic views of the Champlain Valley and distant mountains.

What are the surface conditions like on Vermont's gravel roads?

Vermont's gravel roads, especially around Middlebury, are known for their varied surfaces. You'll encounter well-maintained gravel, but also rougher sections, including what are sometimes referred to as 'Class 4' roads, which can be unmaintained and challenging. These conditions are part of the authentic gravel biking experience in the region.

What is the best time of year for gravel biking in Middlebury?

The best time for gravel biking in Middlebury is typically from spring through autumn. Spring offers lush greenery, while autumn provides stunning fall foliage. Summers are also popular, but be prepared for warmer temperatures. Winter can be challenging due to snow and ice, though some areas might be suitable for fat biking.

Is parking available at trailheads in Middlebury?

While specific trailhead parking details vary by route, Middlebury, as a community that embraces outdoor recreation, generally offers accessible parking options in and around the town, including near popular starting points for cycling routes. It's advisable to check specific route details for the most convenient parking.

Do I need a permit to ride gravel roads in Vermont?

Generally, no specific permits are required for recreational gravel biking on public roads and designated trails in Vermont. However, always respect private property and adhere to any posted signs or local regulations, especially when riding through agricultural areas or near conserved lands.

Are dogs allowed on gravel bike trails in Middlebury?

Many outdoor areas in Vermont, including some gravel roads and multi-use trails, are dog-friendly. However, regulations can vary. It's best to keep dogs on a leash and ensure you clean up after them. Always check specific trail guidelines or local signage for the most accurate information regarding pets.

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