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Routes
Road cycling routes
United States
Vermont
Addison County

Middlebury

The best road cycling routes around Middlebury

5.0

(3)

480

riders

26

rides

Road cycling routes around Middlebury, Vermont, traverse a diverse landscape that includes the expansive farmlands of the Champlain Valley and the challenging ascents of the Green Mountains. The region features significant mountain gaps like Middlebury Gap and Brandon Gap, offering varied terrain for cyclists. Routes often extend towards Lake Champlain, providing views of the lake and distant Adirondack Mountains. Otter Creek flows through the town, adding a natural feature to urban sections of some routes.

Best road cycling routes around…

Last updated: July 7, 2026

9

riders

#1.

Chimney Point loop

54.5km

02:22

490m

490m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

4

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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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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 in Middlebury?

Middlebury offers over 25 road cycling routes, catering to various skill levels, from moderate loops to challenging mountain ascents.

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

Road cycling in Middlebury features a diverse landscape, from the rolling farmlands of the Champlain Valley to challenging ascents in the Green Mountains, including iconic passes like Middlebury Gap and Brandon Gap. Many routes also offer views towards Lake Champlain and the distant Adirondacks.

Are there road cycling routes suitable for beginners in Middlebury?

Yes, Middlebury has several routes suitable for those new to road cycling. While specific 'easy' routes aren't detailed, the region's diverse network includes options with less elevation gain, particularly in the Champlain Valley. You can find 5 easy routes listed on komoot.

What are some challenging road cycling routes for experienced riders?

Experienced riders seeking a challenge can explore routes that tackle the region's mountain gaps. The Appalachian Gap – Middlebury Gap loop from Middlebury is a demanding 72.9-mile route with significant elevation gain, often taking over 5 hours to complete. Another challenging option is the Middlebury Falls – Middlebury Gap loop from Middlebury.

Can I find loop routes for road cycling in Middlebury?

Yes, many road cycling routes in Middlebury are designed as loops, allowing you to start and end in the same location. Examples include the Chimney Point loop, which offers views towards Lake Champlain, and the Forest Dale & Brandon loop through rolling farmlands.

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

The best time for road cycling in Middlebury is typically from late spring through early fall (May to October), when the weather is mild, and the scenery is vibrant. This period avoids winter conditions and offers comfortable temperatures for longer rides.

Are there any scenic attractions or landmarks to see along the road cycling routes?

Yes, many routes pass by notable attractions. You can see the picturesque Middlebury Falls right in town, or cycle past the historic Pulp Mill Covered Bridge. The region also features views of Lake Champlain and the Green Mountains.

Where can I find parking for road cycling routes in Middlebury?

Middlebury, being a bike-friendly town, offers various parking options. Many routes start from the town center, where public parking is available. For routes starting outside the town, look for designated parking areas near trailheads or local parks. Always check local regulations.

Are there options for public transportation to access cycling routes in Middlebury?

While Middlebury has local public transportation, direct access to specific cycling route starting points via public transport might be limited. Most cyclists typically drive to a convenient starting point in or around Middlebury. Consider checking local bus schedules for connections within Addison County if planning to use public transport.

Are there any cafes or places to stop for refreshments along the routes?

Middlebury's charming downtown area, including Main Street, offers several cafes, restaurants, and pubs perfect for a pre-ride coffee or a post-ride meal. Many routes also pass through smaller towns or villages with local establishments where cyclists can refuel.

What do other cyclists say about road cycling in Middlebury?

The road cycling routes in Middlebury are highly rated by the komoot community, with an average score of 5.0 stars from several reviews. Cyclists often praise the diverse terrain, the stunning views of the Green Mountains and Lake Champlain, and the well-maintained roads through rolling farmlands.

Are there family-friendly road cycling options in Middlebury?

For families, routes with less traffic and flatter terrain are ideal. While specific family-friendly road cycling routes aren't highlighted, the expansive Champlain Valley offers bucolic roads suitable for a more relaxed pace. Always check route details for elevation and traffic levels to ensure suitability for your family.

What are the typical distances and durations of road cycling routes in Middlebury?

Road cycling routes in Middlebury vary significantly in length and duration. You can find moderate paths like the Huntington Falls – Pulp Mill Covered Bridge loop from Middlebury, which is about 24 miles (39 km) and takes around 1 hour 45 minutes, up to challenging routes over 70 miles (117 km) that can take over 5 hours.

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