Date: August 15, 2026
Location: West Windsor & Southern Vermont, USA
Distance: ~55 miles (~88 km)
Elevation Gain: ~7,000 ft (~2,135 m)
Event Type: Unsupported Gravel Adventure Ride
Event Description
Vermont Overland – The Overland Bike is a celebrated gravel cycling event set amidst the rolling hills, forest corridors, and unmaintained dirt roads of southern Vermont. Known as one of North America’s classic adventure rides, The Overland blends rugged terrain with scenic pastoral landscapes, creating a course that challenges riders while showcasing the unique character of Vermont’s countryside.
This iconic event covers approximately 55 miles of open dirt and gravel roads that connect historic towns, scenic climbs, and remote public corridors. The course features a mix of rolling gravel sectors, short steep hills, and unmaintained “Vermont pavé” — old dirt roads and ancient public through-ways that provide both challenge and reward. With about 7,000 feet of climbing, The Overland demands endurance, bike handling, and a spirit of adventure from every participant.
The bike ride is held in conjunction with a wider celebration of all-surface exploration and community energy. Riders gather in West Windsor, a gateway to Vermont’s gravel network and rural charm, before heading out into the surrounding countryside. Along the route, well-placed support stations, scenic views, and a vibrant sense of camaraderie underscore the experience of riding together across a landscape shaped by natural beauty and agricultural heritage.
The Overland is designed not just as a race but as an adventure — a day where the joy of riding hard on varied terrain meets the satisfaction of exploring terrain less ridden, meeting local communities, and reconnecting with the roots of gravel cycling culture. It’s a ride that resonates with both seasoned gravel riders and those seeking a memorable challenge set amidst Vermont’s iconic terrain.
Vermont Overland – The Overland Bike: raw gravel roads, rolling hills, unforgettable scenery, and a true celebration of overland adventure.
Click here to see more inspiring North American gravel events
- 26/08/2023
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- 26/08/2023
- 17:00
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- https://www.vermontoverland.com/
- Brownsville, West Windsor, Vermont, USA