3.3
(4)
33
riders
10
rides
Gravel biking around East Middlebury offers routes through a landscape characterized by rolling hills, dense woodlands, and scenic river valleys. The region features a mix of unpaved roads and forest paths, providing varied terrain for gravel cyclists. Routes often incorporate natural features like Middlebury Falls and historic elements such as covered bridges. The elevation changes across the area contribute to a dynamic riding experience.
Last updated: May 28, 2026
4
riders
49.8km
03:04
710m
710m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.0
(1)
4
riders
29.7km
01:44
300m
300m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3.0
(1)
4
riders
48.0km
02:54
660m
660m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
46.6km
02:55
730m
730m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.0
(1)
3
riders
29.0km
01:39
320m
320m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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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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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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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 offers a selection of 10 gravel bike routes, providing a diverse range of options for cyclists. These routes are rated by the komoot community with an average score of 3.0 stars.
The region is particularly beautiful during the fall, offering stunning foliage as you ride through dense woodlands. Spring and summer also provide pleasant conditions for exploring the rolling hills and river valleys.
While East Middlebury's routes generally feature rolling hills and varied terrain, there are moderate options available. For a good introduction, consider the Middlebury Falls – Pulp Mill Covered Bridge loop from Middlebury, which is 18.6 miles long and combines natural scenery with a historic landmark.
You can expect a mix of unpaved roads and forest paths, characterized by rolling hills, dense woodlands, and scenic river valleys. The elevation changes across the area contribute to a dynamic riding experience, from steady climbs to more challenging ascents.
Yes, East Middlebury has several difficult routes for those seeking a challenge. The Middlebury Falls – Middlebury College Quad loop from Middlebury is a 31.0-mile difficult trail with significant elevation gain and diverse terrain, often taking nearly four hours to complete.
Many routes incorporate natural features and historic elements. You might encounter the beautiful Middlebury Falls, or the historic Pulp Mill Covered Bridge. Some trails also pass by the Middlebury College Quad, offering a glimpse of the local campus.
Parking is generally available in and around Middlebury, which serves as a common starting point for many of the gravel bike routes. Specific parking details can often be found on individual route pages on komoot, or by checking local town resources.
For families looking for a moderate ride, routes that are shorter in distance and have less extreme elevation changes would be ideal. The Main Street – Middlebury Falls loop from Middlebury, at 18.0 miles, offers a manageable distance and moderate difficulty, making it a good option for active families.
Many routes start or pass through Middlebury, where you'll find various cafes, restaurants, and shops. While specific cafes directly on the unpaved sections of trails might be limited, planning your route to include stops in town is easily done. The Main Street area in Middlebury is a good place to find amenities.
The routes in East Middlebury feature significant elevation changes due to the region's rolling hills. For example, a difficult route like the Willmarth Woods loop from Middlebury can involve over 650 meters of ascent, while moderate routes typically have around 200-300 meters of elevation gain.
Generally, permits are not required for gravel biking on the public roads and designated trails in the East Middlebury area. However, it's always advisable to respect private property and check for any specific local regulations or temporary closures before heading out.
Ride durations vary significantly based on the route's length and difficulty, as well as your pace. Moderate routes, such as the Middlebury College Quad – Middlebury Falls loop from Middlebury (24.1 miles), can take around 3 hours, while longer, more difficult trails might require closer to 4-5 hours to complete.
The area is highly rated by the komoot community, with an average score of 3.0 stars from over 4 reviews. Reviewers often praise the diverse terrain, the blend of natural scenery with historic elements like covered bridges, and the dynamic riding experience offered by the rolling hills and varied paths.


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