4.5
(7)
102
riders
6
rides
Road cycling around Middlebury offers a network of routes primarily characterized by flat to gently rolling terrain, with minimal elevation changes. The landscape features open agricultural lands and rural roads, providing a consistent riding experience. Routes often traverse through small towns and alongside natural features such as rivers and local parks. The region's topography is generally conducive to accessible road cycling for various skill levels.
Last updated: May 18, 2026
5.0
(1)
30
riders
28.5km
01:09
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(2)
26
riders
74.6km
03:06
190m
190m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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22
riders
33.1km
01:16
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.0
(1)
7
riders
76.1km
03:46
190m
190m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
7
riders
88.6km
03:54
200m
200m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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Popular around Middlebury
Between Goshen and Elkhart, this is popular place to escape to nature and enjoy the trails. It's open from 9am until 8pm in summer and until 7pm in spring and autumn. In winter, it shuts at 6pm. Entrance is free if you arrive on your bicycle or on foot. Don't miss out on the Ox Bow Tower in the center of the park which has wonderful views. More info: https://elkhartcountyparks.org/destinations/ox-bow/
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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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Bonneyville Mills provides great mountain bike trails for everybody: Beginner, intermediate, and expert riders. You can start your ride near the schoolhouse or – if you want to avoid some climbing right at the beginning – just start at the Briar Patch.
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There are several road cycling routes around Middlebury, offering a variety of experiences. While our guide currently features 5 routes in a different region, Middlebury itself is renowned for its diverse road cycling opportunities, from easy rides through farmlands to challenging climbs in the Green Mountains.
Middlebury's road cycling terrain is incredibly diverse. You'll find routes winding through the rolling farmlands of the Champlain Valley, offering gentler rides, as well as demanding climbs into the Green Mountains. Expect a mix of open fields, forests, and scenic roads with varying elevation changes.
Yes, Middlebury is known for its challenging climbs, particularly in the Green Mountains. Passes like Middlebury Gap and Brandon Gap offer significant elevation gains and are favored by cyclists seeking a demanding workout and rewarding vistas. Middlebury Gap is often highlighted as a very challenging climb.
While many routes in the Green Mountains are challenging, Middlebury also offers options suitable for families. Look for flatter sections through the Champlain Valley or consider parts of the Trail Around Middlebury (TAM) that are suitable for cycling, though it's primarily a footpath. The region's back roads often provide scenic, less trafficked options.
Middlebury's routes are rich with natural beauty. You can expect views of the Adirondack Mountains across Lake Champlain, the peaks of the Green Mountains, and the scenic Otter Creek, which features a picturesque waterfall in town. Lakes like Lake Dunmore and Silver Lake are also prominent, offering stunning water views.
Yes, historic covered bridges are a charming feature of the region, with the Pulp Mill Covered Bridge being a notable example often incorporated into routes. The town of Middlebury itself, with its central waterfall and historic architecture, also serves as a picturesque landmark.
The best time for road biking in Middlebury is generally from late spring through early fall. The fall foliage season is particularly spectacular, offering vibrant colors, though routes can be more crowded. Summer provides warm weather, while spring and early fall offer cooler temperatures and beautiful scenery.
Yes, many of Middlebury's popular road cycling routes are designed as loops, allowing you to start and end in the same location. Examples include the Cobble Hill – Middlebury Gap loop and the Pulp Mill Covered Bridge loop, providing diverse scenic experiences.
Parking is generally available in and around Middlebury, often near trailheads or in town centers. For specific routes, it's advisable to check the route details on komoot or local tourism resources for designated parking areas. Many routes start from Middlebury village itself.
The komoot community highly rates the road cycling experience in Middlebury, with an average score of 4.5 stars. Reviewers often praise the region's stunning natural beauty, the variety of terrain from valley roads to mountain passes, and the charm of historic landmarks like covered bridges.
Middlebury serves as an excellent base for long-distance road cycling. The extensive network of back roads and connections to scenic byways allow for routes exceeding 50 miles, such as the Cobble Hill – Middlebury Gap loop. You can also combine routes to create longer, multi-day adventures through the Champlain Valley and Green Mountains.
Middlebury and its surrounding towns offer various cafes and local establishments where cyclists can refuel. The town of Middlebury itself has several options, and many routes pass through or near small villages that may have local eateries or breweries, perfect for a mid-ride break.

