5.0
(3)
499
riders
34
rides
If you've ever tried to plan road cycling around East Middlebury, you know how quickly the options can become overwhelming. With so many roads crisscrossing the Green Mountains and Champlain Valley, it's tough to tell which routes are genuinely worth your time and effort, and which are just filler. We get it — nobody wants to waste precious saddle time on a mediocre ride.
That's why we've done the legwork for you. Our komoot community has ridden, mapped, and reviewed…
Last updated: June 1, 2026
9
riders
54.5km
02:22
490m
490m
The Chimney Point loop offers road cyclists a truly scenic journey, combining the natural beauty of Lake Champlain with the dramatic backdrop of the Adirondack Mountains. You'll enjoy expansive water…
4
riders
65.6km
02:47
550m
560m
The Forest Dale & Brandon loop offers a delightful journey through Vermont's charming countryside, perfect for a scenic road cycling adventure. You'll wind through picturesque villages like Brandon, known for…

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178
riders
119km
05:47
1,680m
1,680m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
90
riders
97.8km
04:41
1,270m
1,270m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
34
riders
39.3km
01:45
390m
390m
The Huntington Falls – Pulp Mill Covered Bridge loop from Middlebury offers a delightful road cycling adventure through Vermont's picturesque Addison County. You'll pedal past rolling farmlands and along river…
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The site chronicles millennia of local history, from indigenous cultures to the French-Indian War and early America. They have a lot of interesting artefacts, but the hours can be odd so it's best to check the website before your ride if you are planning to stop by. The views of Lake Champlain, the bridge, and Fort St. Frederic across the water make this a pretty remarkable spot to visit.
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Forest Dale is a small community with a church, post office, and historic early-1800s ironworks, the ruins of which can be found on the northeast side of town. The Junction Store & Deli is open 7am-7pm most days if you want to grab a bite before continuing on your ride.
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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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A very beautiful area along farms
5
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Extremely hilly, sounds of nature, lot's to see & experience. Downhills are well worth the climbs. You definitely need to have some rides/climbing in your season. Update 7/26/25 Still crazy hilly & and punchy. However, the downhill runs are amazing..😉
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Brandon Gap is a tall mountain pass in the green mountains on Gap Road. This is a challenging climb in a beautiful area in the green mountains. The Long Trail crosses the road right at the summit of the pass, so be on the lookout for thru-hikers as you ride past!
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Middlebury Gap is a mountain pass in Vermont's Green Mountains and a great, very challenging climb for any rider. It divides two different drainage areas with the Robbins Branch flowing southeast into the White River, and the South Branch into Middlebury River, which into Otter Creek, connecting to Lake Champlain. The Long Trail, a 272-mile hiking route traversing Vermont, runs through here, passing between Worth Mountain and Boyce Mountain. The Breadloaf Wilderness lies to the north, while Middlebury College Snow Bowl and Joseph Battell Wilderness are nearby to the south.
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East Middlebury offers a diverse selection of over 30 road cycling routes. These include 8 easy routes, 22 moderate routes, and 3 challenging routes, catering to various skill levels.
You can expect a mix of terrain, from picturesque paved surfaces to challenging mountain passes. The region is known for significant elevation changes, particularly around the Middlebury Gap, which features a notable 6-mile climb. Many routes utilize scenic back roads, offering breathtaking vistas of the Green Mountains.
Yes, East Middlebury has 8 routes suitable for beginners. While specific easy routes are not detailed here, the region offers options that allow for a more relaxed pace, often featuring primarily paved surfaces and less demanding elevation profiles.
Experienced riders seeking a challenge can explore routes with significant elevation gain. A prime example is the Appalachian Gap – Middlebury Gap loop from Middlebury, which covers over 70 miles and includes challenging mountain passes. Another demanding option is the Middlebury Falls – Middlebury Gap loop from Middlebury, also featuring substantial climbs.
Yes, many road cycling routes around East Middlebury are designed as loops. Popular options include the Chimney Point loop and the Forest Dale & Brandon loop, which offer varied distances and scenic views.
The routes often pass by significant landmarks and natural features. You might encounter the historic Pulp Mill Covered Bridge spanning Otter Creek, or the dramatic Middlebury Falls. The Green Mountain National Forest is also a prominent feature, offering expansive natural beauty.
The warmer months, particularly summer and early fall, are ideal for road cycling in East Middlebury. During this time, the weather is generally pleasant, and the natural beauty of the Green Mountains is at its peak, offering lush landscapes and comfortable riding conditions.
While specific family-friendly routes are not highlighted, the region does offer 8 easy routes that could be suitable for families. These routes typically feature less elevation gain and are often on paved surfaces, providing a more relaxed experience for all ages.
The road cycling routes in East Middlebury are highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the challenging mountain passes, the scenic back roads, and the overall natural beauty of the Green Mountains, which provide a rewarding experience for various ability levels.
Yes, several routes offer glimpses into the region's history and notable points of interest. For instance, the Huntington Falls – Pulp Mill Covered Bridge loop from Middlebury takes you past the iconic Pulp Mill Covered Bridge. The Middlebury Gap itself holds historical significance as a vital route through the Green Mountains.
Route distances vary significantly to accommodate different preferences. You can find moderate routes like the Chimney Point loop at approximately 34 miles (54.5 km), or longer, more challenging rides such as the Appalachian Gap – Middlebury Gap loop from Middlebury, which spans over 70 miles (117.4 km).
Absolutely. The East Middlebury area is renowned for its breathtaking vistas, especially along routes that traverse the Green Mountains and its passes. Cyclists can expect numerous scenic viewpoints offering panoramic views of the surrounding natural landscape and valleys.


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