When Sat, Aug 15, 9am -3pm Source Vermont Overland Calendar iCal Download Description The Overland is a 55-mile (distances fluctuate based on years/course) dirt road bicycle ride featuring close to 7,000 feet of climbing, eight sectors of Class4 Roads (unmaintained ancient public through-ways), two sag stops, a magnificently scenic route and an awesome party afterwards. It’s the ultimate overland adventure ride. Open dirt roads, amazing scenery and an epic course unlike any you’ve ever ridden before, all within a beautiful Vermont pastoral setting. The purpose of this race is to promote the wonderful world of overland adventure riding and to benefit the Reading/West Windsor Food Shelf, Ascutney Outdoors and WAMBA–all integral organizations in the event’s host towns of Reading/West Windsor/Woodstock. Saturday, August 15th, 2026 Ascutney Outdoors, Ski Tow Road, West Windsor, Vermont 55 Miles, 7,000' climbing 9 AM Start Race is limited to 1000 riders. Registration Opens on January 1st, 2026 at 9 AM. Juniors race for FREE. Always. West Windsor locals have a guaranteed spot. Contact us with your address. We save space for women.