The Vermont Overland Trail Run 2026 is not a half marathon – it is not an Ultra – it’s something completely different. Challenge yourself over 15 miles and 2,600 feet across an all-surface course covering the best of the best in West Windsor, VT. The Vermont Overland TRAIL Run 2026 is an open run so that anyone can enter. Everyone is welcomed and celebrated, from pro runners going for the $5k in awards to folks just wanting to find a new challenge. The purpose of this event produced by the Vermont Overland team is to promote overland running (a mix of hard, cross country, and trail surfaces) and to raise funds for the benefit of both Ascutney Outdoors and Ascutney Trails Association, two local organizations that work tirelessly on their vision for a new era of recreation and conservation at Mount Ascutney.

The event features a communal start at 9 AM, where runners tackle either a 15-mile or 5-mile course. Two route options will be available at The Vermont Overland Trail, a 15-mile Overland TRAIL course and a 4-mile Overland PATH course. Along the course, participants can rely on multiple Aid Stations and a Water Stop equipped with water, Untapped Maple fuel, snacks from The Brownsville Butcher & Pantry, and volunteer support. Despite these provisions, runners are advised to come prepared to be self-sufficient.

Stick around for a great party after the race with food and beverage provided by local farm-based business, The Brownsville Butcher & Pantry. Notably, a $5,000 prize purse is available for the 15-mile race and is equally distributed between male and female top finishers.

Remember the Overland TROPHY, it is eligible for athletes who compete in both running and cycling events. The top 3 participants win bragging rights to being the most well-rounded athletes with the ability to traverse a landscape efficiently no matter the mode, in addition to some cool custom Vermont Overland prizes.

This is the second annual trail event coming from Vermont Overland. It draws inspiration from The Overland, one of the most popular and longest-running gravel cycling events in the US, which Strambecco rates as one of the Best Gravel Cycling Race Events in New England and one of the Best Cycling Race Events in Vermont. The organizers’ mission is to promote adventure travel and they got started by believing in the transformative power of all-surface exploration – as they say, it’s the best way to race, run, ride, and experience a landscape.