Conquer Vermont’s rugged dirt roads and epic climbs for charity.

The Overland, held in West Windsor, Vermont, on August 24, 2025, is a 55-mile dirt road adventure race that takes cyclists over 7,000 feet of elevation gain through scenic countryside and over rugged, unmaintained Class 4 public roads. The event creates a true adventure for riders of all skill levels while benefitting local organizations like the Reading/West Windsor Food Shelf and Ascutney Outdoors with proceeds from registration.

The course covers 55 miles of mixed dirt and gravel roads, including eight challenging sectors of Class 4 (unmaintained) roads across Vermont’s rolling landscape. Riders start and finish at Ascutney Outdoors in West Windsor.

• Post-race party with local food and drinks
• Overland TROPHY: Combine results with the 15-mile trail run for special prizes
• Limited to 1,000 riders, prioritizing women and West Windsor locals
• Scenic Vermont countryside and community-driven atmosphere
• Supports local charities like the Reading/West Windsor Food Shelf and Ascutney Outdoors