4.5
(12)
113
riders
3
rides
Touring cycling around Middlebury offers diverse routes through picturesque landscapes. The region is characterized by the rolling hills and farmlands of the Champlain Valley, with the Green Mountains providing a scenic backdrop to the east. Cyclists can explore routes along the Otter Creek and discover charming back roads, making it an ideal destination for varied cycling experiences.
Last updated: May 21, 2026
69.1km
03:58
160m
160m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
42
riders
30.7km
01:44
70m
70m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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38
riders
28.3km
01:37
80m
80m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(5)
20
riders
20.2km
01:10
60m
60m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
6
riders
25.5km
01:28
90m
90m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Middlebury
Goshan was named so in connection with the Bible. It was the name given to a region of Egypt where the Hebrews resided during their stay. Today it is a dynamic city, the seat of Elkhart County.
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The Pumpkinvine Nature Trail is a cycle greenway path which follows the old route of the Pumpkin Vine Railway. There is a website dedicated to this bike path that connects historic cities in the state of Indiana. for more information see the following website : https://pumpkinvine.org
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This small city in Indiana attracts nostalgic folks as well as collectors. Shipshewana indeed has the largest flea market in this state, but it is also an Amish enclave. Amish buggy are offering tourist rides in town. Vintage cars used to attract a lot of people. The collection of Hudson-produced vehicles owned by Eldon Hostetler was located in the Shipshewana town center, across from the auction grounds. Unfortunately after mister and miss Hostetler passed away, the town of Shipshewana decided to close the museum in January 2018. The collection was sold at auction on August 4, 2018. The town also has a working bison ranch and a beautiful environment with lakes and meadows.
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Middlebury offers a diverse range of touring cycling experiences, from leisurely rides through the fertile Champlain Valley farmlands to more challenging routes with rolling hills and scenic back roads. You'll find paths along the Otter Creek and routes with views of the majestic Green Mountains to the east and the Adirondacks to the west.
Yes, Middlebury has several easy touring routes perfect for beginners or families. For instance, the Shipshewana loop from Middlebury is an easy 19.8-mile path guiding cyclists through picturesque farmlands. Another great option is the Covered Bridge loop from Shipshewana, a 17.5-mile trail featuring scenic rural areas and historic covered bridges.
For those seeking a longer ride, the Pumpkinvine Nature Trail offers a moderate 42.9-mile experience traversing varied rural landscapes. While the immediate guide focuses on these routes, the broader Middlebury region, particularly the Green Mountains, provides significant climbs like Middlebury Gap for advanced cyclists.
Absolutely! Many touring routes in Middlebury are designed as loops, allowing you to start and end in the same location. Examples include the Shipshewana loop from Middlebury, the Covered Bridge loop from Shipshewana, and the Goshen – Pumpkinvine Nature Trail loop from Mooey's Ice Cream Shop.
Middlebury's touring routes offer numerous scenic vistas. You'll enjoy expansive views of the Green Mountains to the east and the Adirondack Mountains in New York to the west, especially across the Champlain Valley's farmlands. The Otter Creek, with the notable Middlebury Falls right in town, also provides a beautiful natural feature. Historic covered bridges, like the Pulp Mill Covered Bridge, are also picturesque sights along some routes.
The best time for touring cycling in Middlebury is typically from late spring through early autumn. During these months, the weather is generally pleasant, and the landscapes are vibrant, whether with spring blossoms, summer greenery, or spectacular fall foliage. Always check local weather and trail conditions before heading out.
Yes, the region is known for its charming covered bridges. The Covered Bridge loop from Shipshewana specifically highlights these historic structures. The Pulp Mill Covered Bridge, one of only two double-lane covered bridges in Vermont, is a notable landmark in the area often included in cycling routes.
You can expect a mix of terrain, primarily characterized by rolling farmlands and scenic back roads in the Champlain Valley. Some routes may include gentle climbs and descents, especially as you approach the foothills of the Green Mountains. Many routes feature a combination of paved and dirt roads, so a gravel bike or a road bike with wider tires is often recommended for optimal comfort.
The touring cycling routes in Middlebury are highly rated by the komoot community, with an average score of 5.0 stars from more than 6 reviews. Cyclists often praise the picturesque farmlands, quiet back roads, and the diverse scenery that includes views of the Green Mountains.
While specific cafes on routes aren't detailed, Middlebury's historic downtown offers unique local shops, art galleries, and restaurants where you can refuel. The region also hosts the annual 'Tour de Farms,' which showcases the local food scene, suggesting that opportunities for local produce and eateries are available, especially in and around towns.
Yes, Middlebury is part of the broader Lake Champlain Bikeways network, with five routes passing directly through the town. This connects Middlebury to extensive regional cycling opportunities, allowing for longer journeys beyond the immediate local loops.
Beyond touring cycling, Middlebury is a hub for various outdoor activities. You can explore the Green Mountain National Forest, hike the Trail Around Middlebury (TAM), or visit Snake Mountain for panoramic views. Water activities like kayaking and swimming are popular at Lake Dunmore and Branbury State Park. The Robert Frost Interpretive Trail also offers a unique nature and literature experience.


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