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Vermont
Addison County
Middlebury

Main Street

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Main Street

Gravel riding

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Road cycling

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  • Location: Middlebury, Addison County, Vermont, United States

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    June 25, 2025

    Road cycling

    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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    Nearby routes

    Best routes near Main Street

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    4

    riders

    #1.

    Forest Dale & Brandon loop

    65.6km

    02:47

    550m

    560m

    The Forest Dale & Brandon loop offers a delightful journey through Vermont's charming countryside, perfect for a scenic road cycling adventure. You'll wind through picturesque villages like Brandon, known for its historic buildings, and Forest Dale, where you can spot the impressive 1856 smokestack and blast furnace. Expect a mix of low, rolling hills and some more sustained climbs, all on generally well-maintained paved roads, providing a pleasant and varied ride through agricultural lands and glimpses of the Green Mountains.

    This moderate 40.7-mile (65.6 km) road cycling route, with 1817 feet (554 metres) of elevation gain, typically takes about 2 hours and 47 minutes to complete. You can start your ride from either Brandon or Forest Dale, both offering convenient access and local amenities. Spring, summer, and fall are the best seasons to tackle this route, allowing you to enjoy the vibrant foliage and comfortable temperatures.

    What makes this route stand out is its blend of historic charm and natural beauty, showcasing the best of central Vermont. While the main loop focuses on manageable terrain, the region also offers the significantly more challenging Brandon Gap climb nearby for those seeking a serious test of endurance. This loop provides a fantastic way to explore the area's heritage and expansive views without committing to extreme mountain gradients.

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    Moderate
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    The Middlebury College Quad – Middlebury Falls loop from Middlebury is a challenging racebike route that offers a deep dive into Vermont's scenic beauty and charming town life. You'll experience the unique 20-foot Middlebury Falls on Otter Creek, visible from the town's Main Street, and cycle past the historic Middlebury College Quad. Beyond the urban charm, the route unfolds into diverse landscapes of farmlands, orchards, and distant mountain views, providing a rich visual tapestry for the entire journey.

    This difficult route covers an impressive 74.1 miles (119.3 km) with a substantial 5504 feet (1677 metres) of elevation gain, typically taking around 5 hours and 46 minutes to complete. It's designed for experienced road cyclists looking for a demanding day in the saddle. Parking is available in downtown Middlebury, where you can also find cafes and shops; starting early is advisable to make the most of the daylight for this extensive ride.

    What makes this route stand out is its blend of natural beauty and cultural landmarks, offering more than just a workout. It combines the picturesque Middlebury Falls and the academic setting of Middlebury College with the broader, scenic Vermont countryside. The area is particularly stunning during the fall foliage season, making it a prime destination for those seeking vibrant autumn cycling experiences.

    Hard
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    Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

    Hard

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    Elevation 110 m

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    Sunday 14 June

    32°C

    17°C

    50 %

    Additional weather tips

    Max wind speed: 24.0 km/h

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    Location: Middlebury, Addison County, Vermont, United States

    Other Popular Places to Check Out

    Trail Around Middlebury (Western Segment)

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