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Routes
Cycling routes
United States
Vermont
Addison County

Middlebury

The best cycling routes around Middlebury

4.5

(4)

52

riders

18

rides

Touring cycling around Middlebury, Vermont, is characterized by a diverse landscape that includes the rolling farmlands of the Champlain Valley and the challenging terrain of the Green Mountains. The region features significant waterways like Otter Creek, which flows through the town, and offers routes with varied elevation profiles. Cyclists can find paths through forested areas, alongside rivers, and across open agricultural lands, providing a range of experiences from gentle rides to demanding climbs.

Best touring cycling routes around Middlebury

  • The most popular touring cycling route is Cobble Hill – Middlebury Gap loop from East Middlebury, a 49.0 miles (78.9 km) difficult trail that takes about 5 hours 8 minutes to complete, featuring significant elevation gains through the Green Mountains.
  • Another top favourite among local touring cyclists is Pulp Mill Covered Bridge loop from Middlebury, a moderate 24.0 miles (38.6 km) path. This route offers scenic views and passes by the historic Pulp Mill Covered Bridge.
  • Local touring cyclists also love the Middlebury Water Supply loop from Green Mountain Family Campground, a 20.4 miles (32.8 km) trail leading through forested areas with notable elevation, often completed in about 2 hours 59 minutes.
  • Touring cycling around Middlebury is defined by the Green Mountains, the Champlain Valley's farmlands, and the Otter Creek, offering a mix of challenging climbs and scenic, flatter sections. The network provides options for easy, moderate, and difficult routes, catering to various ability levels.
  • The routes in Middlebury are highly rated by the komoot community with an average score of 4.7 stars from 3 reviews. More than 40 touring cyclists have used komoot to explore Middlebury's varied terrain.

Last updated: April 27, 2026

10

riders

#1.

Brandon Gap – Rochester loop from East Middlebury

79.3km

05:10

1,120m

1,120m

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

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Hard

5.0

(1)

7

riders

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

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

Hard

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

Hard

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

Moderate
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Popular around Middlebury

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Road Cycling Routes around Middlebury

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Gravel biking around Middlebury

Tips from the Community

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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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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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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Lisa
February 25, 2024, Warren Falls

You'll have to hop off your bike if you want to visit Warren Falls, but it's worth the short walk to check out this series of cascades and popular swimming holes.

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Alex
January 22, 2024, Rochester

Rochester welcomes visitors with its quintessential New England charm. Nestled amid picturesque mountains, the town offers outdoor adventures, artisan shops, and local eateries. Explore the scenic Green Mountain National Forest, discover charming boutiques, and savor the hospitality of this Vermont gem.

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Frequently Asked Questions

How many touring cycling routes are available around Middlebury?

There are over 15 touring cycling routes available around Middlebury, catering to various skill levels. These include 1 easy route, 10 moderate routes, and 5 difficult routes, offering a diverse range of experiences from gentle rides through farmlands to challenging climbs in the Green Mountains.

What types of terrain can I expect on touring cycling routes in Middlebury?

Middlebury's touring cycling routes offer a diverse landscape. You can expect to ride through the gently rolling farmlands of the Champlain Valley, alongside waterways like Otter Creek, and tackle challenging ascents in the Green Mountains, such as the Middlebury Gap. Routes often feature a mix of paved roads, forested paths, and scenic agricultural lands.

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

The best time for touring cycling in Middlebury is generally from late spring through early fall. The fall foliage season is particularly vibrant, offering stunning mountain views. However, routes like the Middlebury Gap can be demanding, so checking local conditions is always recommended, especially during shoulder seasons.

Are there family-friendly touring cycling routes in Middlebury?

Yes, Middlebury offers routes suitable for families and those seeking easier rides. While the guide highlights more challenging options, the region's diverse network includes paths through farmlands and along Otter Creek that are less strenuous. The Trail Around Middlebury (TAM), though not exclusively a touring cycling route, provides an 18-mile loop around town that connects conserved properties and local landmarks, offering a gentler experience.

Can I find routes that pass by waterfalls or other natural features?

Absolutely. Several routes incorporate natural features. For instance, the Middlebury Falls – Middlebury College Quad loop from Middlebury passes by the scenic Middlebury Falls, a 20-foot waterfall right in the center of town. Other routes follow Otter Creek, providing scenic views of the waterway, and some venture into forested areas like those found on the Middlebury Water Supply loop from Green Mountain Family Campground.

Are there any historic landmarks or points of interest along the cycling routes?

Yes, Middlebury is rich in history and charm. A notable landmark is the Pulp Mill Covered Bridge, which you can experience on the Pulp Mill Covered Bridge loop from Middlebury. Many routes also pass through the quaint downtown area, offering glimpses of historic architecture and the vibrant Main Street. The Middlebury College Quad is another point of interest featured on routes like the Middlebury Falls – Middlebury College Quad loop from Middlebury.

Are there circular touring cycling routes around Middlebury?

Many of the touring cycling routes around Middlebury are designed as loops, allowing you to start and end in the same location. Examples include the challenging Cobble Hill – Middlebury Gap loop from East Middlebury, the scenic Pulp Mill Covered Bridge loop from Middlebury, and the forested Middlebury Water Supply loop from Green Mountain Family Campground.

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

Parking is generally available in and around Middlebury. Many routes start from locations with public parking, such as town centers or designated trailheads. For routes originating from specific campgrounds or parks, parking facilities are usually provided. It's advisable to check the starting point of your chosen route for specific parking information.

What do other touring cyclists enjoy the most about touring cycling in Middlebury?

The touring cycling experience in Middlebury is highly rated by the komoot community, with an average score of 4.7 stars from 3 reviews. Cyclists often praise the diverse terrain, from the challenging climbs of the Green Mountains to the picturesque farmlands of the Champlain Valley, and the opportunity to discover historic landmarks and natural beauty like the Middlebury Falls.

Are there any easy touring cycling routes for beginners in Middlebury?

Yes, Middlebury offers at least one easy touring cycling route, and several moderate options that can be suitable for beginners looking for a less strenuous ride. These routes typically feature gentler gradients and pass through the scenic Champlain Valley or along Otter Creek, providing a pleasant introduction to touring cycling in the area.

Can I combine touring cycling with other activities like visiting cafes or pubs?

Middlebury is known for its charming downtown, which offers a variety of unique shops, cafes, and restaurants. Many cycling routes pass through or near the town center, making it easy to take a break and enjoy local hospitality. The town's vibrant atmosphere provides pleasant opportunities to refuel and relax during your tour.

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