5.0
(2)
44
riders
18
rides
Touring cycling around East Middlebury, Vermont, is characterized by diverse landscapes, ranging from the challenging ascents of the Green Mountains to the scenic, rolling terrain of the Champlain Valley. The region features significant elevation gains in mountain passes and gentler routes along bucolic roads that wind past farms and historic towns. Otter Creek and various lakes are often integrated into cycling routes, offering varied natural backdrops.
Last updated: May 13, 2026
10
riders
79.3km
05:10
1,120m
1,120m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
7
riders
38.6km
02:24
390m
390m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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6
riders
117km
07:41
1,630m
1,630m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
30.3km
02:41
500m
500m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
5
riders
17.3km
01:10
130m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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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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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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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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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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A stunning natural site featuring a series of cascading falls and inviting swimming holes. It's a popular destination for locals and tourists.
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Granville Notch, or Granville Gulf, is a mountain pass, located in Granville, Vermont on Vermont Route 100. There are creeks, streams, and waterfalls surrounded by lush forests on both sides of the pass, making this a scenic challenge for any cyclist exploring the area.
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East Middlebury offers a diverse cycling landscape. You'll find challenging ascents through the Green Mountains, such as those encountered on the Cobble Hill – Middlebury Gap loop from East Middlebury, which features significant elevation gains. In contrast, the Champlain Valley provides more relaxed rides on bucolic roads winding past farms and historic towns, with routes like the Bike loop from Salisbury offering gentler terrain.
Yes, East Middlebury has routes suitable for beginners. An excellent option is the Bike loop from Branbury State Park. This route is classified as easy, covering 17.3 km with a modest 128 meters of elevation gain, making it a great choice for those new to touring cycling or looking for a more relaxed ride.
While specific family-friendly touring routes are not detailed in the guide, the region offers options that could suit families. The Champlain Valley features many quiet, bucolic roads with less traffic, ideal for a relaxed family outing. Additionally, the Trail Around Middlebury (TAM), an 18-mile loop encircling the village, is suitable for both hiking and biking and connects conserved properties and local landmarks, offering a car-free experience.
Cycling around East Middlebury offers views of several charming landmarks. You can ride past the historic Pulp Mill Covered Bridge, a popular spot for photography, which is featured on the Pulp Mill Covered Bridge loop from Middlebury. Other attractions include the picturesque Middlebury Falls and the historic Main Street of Middlebury, offering a quintessential small New England town experience.
Yes, many touring cycling routes in East 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 and the moderate Pulp Mill Covered Bridge loop from Middlebury. These circular routes make planning your ride convenient.
The best season for touring cycling in East Middlebury is generally from late spring through early autumn. During these months, the weather is typically pleasant, and the landscapes are vibrant, offering lush greenery in summer and stunning foliage in the fall. Winter cycling can be challenging due to snow and ice, especially in the higher elevations of the Green Mountains.
There are over 15 touring cycling routes documented in the East Middlebury area, catering to various skill levels. These routes range from easy, flat rides through the Champlain Valley to difficult, mountainous climbs in the Green Mountains.
The touring cycling routes in East Middlebury are highly rated by the komoot community, with an average score of 5.0 stars. Cyclists often praise the diverse landscapes, from challenging mountain passes to scenic valley roads, and the charm of historic covered bridges and quaint New England towns. The variety of terrain ensures there's something for every rider.
Absolutely. Experienced riders seeking a challenge will find several demanding routes. The Cobble Hill – Middlebury Gap loop from East Middlebury is a difficult 78.9 km route with over 1,100 meters of elevation gain, including the 'very challenging climb' of Middlebury Gap. Another difficult option is the Bike loop from Ripton, covering 38.9 km with over 600 meters of ascent.
While East Middlebury itself is a smaller community, the town of Middlebury, which is central to many routes, does have some local transport options. However, direct public transport access specifically designed for reaching the start points of all touring cycling routes might be limited. It's often most convenient to drive and park near your chosen route's starting point, especially for routes extending into more rural areas.
Parking availability varies by route. For routes starting near Middlebury, you can often find parking within the town or at designated trailheads. For example, routes like the Pulp Mill Covered Bridge loop from Middlebury would likely have parking options in or around Middlebury. For routes originating from state parks or smaller villages like Salisbury or Branbury State Park, dedicated parking areas are usually available at those locations.
Yes, many touring cycling routes in the East Middlebury area pass through or near charming towns and villages where you can find cafes, pubs, and restaurants. Middlebury itself offers a 'quintessential small New England town experience' with local shops and eateries. Villages like Bristol are also known as popular lunch stops on longer cycling tours, providing opportunities to refuel and relax.


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