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Routes
Road cycling routes
United States
Vermont
Addison County

East Middlebury

The best road cycling routes around East Middlebury

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

#1.

Chimney Point loop

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…

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Moderate

4

riders

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…

Moderate
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Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

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…

Moderate
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Tips from the Community

Zachary
June 25, 2025, Chimney Point & State Historic Site

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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Zachary
June 25, 2025, Forest Dale

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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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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Nice little area for break/rest by the river.

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A very beautiful area along farms

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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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Jamie S.
February 26, 2024, Brandon Gap

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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Jamie S.
February 26, 2024, Middlebury Gap

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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Frequently Asked Questions

How many road cycling routes are available around East Middlebury?

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.

What kind of terrain can I expect on road cycling routes in East Middlebury?

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.

Are there any beginner-friendly road cycling routes in East Middlebury?

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.

What are some challenging road cycling routes for experienced riders?

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.

Are there any loop routes for road cycling in the area?

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.

What attractions or landmarks can I see along the road cycling routes?

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.

What is the best time of year for road cycling in East Middlebury?

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.

Are there any family-friendly road cycling options?

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.

What do other road cyclists enjoy most about the routes in East Middlebury?

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.

Are there any routes that pass by historic sites or points of interest?

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.

What are the typical distances for road cycling routes in East Middlebury?

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).

Are there scenic viewpoints along the road cycling routes?

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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