Get ready to experience a uniquely challenging and rewarding running adventure at the Overland Trail race on Sunday, August 16, 2026, in scenic West Windsor, Vermont. This event, hosted at Ascutney Outdoors, offers two distinct distances: the demanding 15-mile "Overland TRAIL" and the spirited 6-mile "Overland Path" option. Unlike a typical half marathon or ultra, the Overland Trail is an "all-surface" event, expertly blending trail, cross-country, and road running across Vermont's rugged and picturesque landscape.

The 15-mile course challenges runners with close to 2,500 feet of elevation gain, earning its reputation as an expert route with a hard physical rating, while the 6-mile option features around 1,000 feet of climbing. Expect breathtaking scenery throughout, traversing diverse terrain that showcases the best of West Windsor. Aid stations on course will provide water, Untapped Maple fuel, and snacks from The Brownsville Butcher & Pantry, though runners are encouraged to be prepared for self-sufficiency. Typical race day conditions in mid-August include highs around 80F and lows near 56F, with a 14% chance of precipitation, creating a truly authentic New England running experience.

What truly sets the Overland Trail apart is its commitment to "all-surface exploration" and a vibrant community atmosphere. For those seeking the ultimate challenge, the Overland Trophy offers an overall competition combining the running race with the 55-mile Overland bicycle race, celebrating well-rounded athletes. With a limited field of 1000 runners, a mass start at 10 AM, and impressive post-race food and drink from local purveyors, this event promises not just a race, but a memorable journey through the heart of Vermont.