The Vermont Overland Trail 2025

Name: The Vermont Overland Trail 2025
Start: 2025-08-23T00:00:00-04:00
End: 2025-08-23T23:59:59-04:00
Location: West Windsor, Vermont

August 23, 2025

Last Updated December 11, 2024

The Vermont Overland Trail 2025 race 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 Overland TRAIL 2025 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.

Below, you will find information on course details, lodging, dining, and other outdoor activities to do while in town for the Vermont Overland Trail.

Event & Course Info

The Overland TRAIL race welcomes all runners seeking a new challenge, from professionals to casual participants. 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. For footwear, while any trail shoes are recommended, participants are encouraged to wear what they find most comfortable.

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.

Area Accommodations & Things to Do

Where to Stay in West Windsor

Get the full Overland experience by planning to camp at and around Ascutney Outdoors by adding this to your registration. There are options to pitch a tent or camp in your car. If you prefer more traditional lodging accommodations, check out Kedron Valley Inn or the Woodstock Inn or the full list of recommended hotels. There are also vacation rentals to choose from, from this stylish guesthouse to this peaceful retreat, perfect for a group participating in The Overland.

Dining in West Windsor

Nestled in the charming embrace of Vermont’s natural beauty, West Windsor offers not only breathtaking landscapes but also a delightful culinary scene that celebrates organic and locally sourced foods. As you explore the town’s quaint streets, you’ll discover a range of dining options, like South Woodstock Country Store and Mon Vert Cafe, that reflect the region’s commitment to sustainability, organic ingredients, and a farm-to-table ethos.

Outdoor Activities around West Windsor

For outdoor athletes and adventure enthusiasts, West Windsor, Vermont, is a haven of possibilities during the entire year. From heart-pounding activities to serene nature explorations, the town and its surroundings offer a diverse range of options that cater to every adrenaline level. Pack your mountain bike to enjoy the Ascutney Trails after the event has concluded. This mountain biking haven offers an extensive network of trails that cater to various skill levels, from beginners to seasoned riders. The diverse terrain includes thrilling descents, technical challenges, and flowy singletrack.

Hiking the Weathersfield Trail to the summit of Mount Ascutney is an ideal choice for those looking for a challenging hike that rewards your efforts with panoramic views that stretch across Vermont and beyond. As you ascend through lush forests and rocky terrain, you’ll experience a true connection with nature. The summit’s observation tower provides a vantage point to admire the surrounding landscapes.

For those who find solace in the water, kayaking or canoeing on the Connecticut River offers a serene and invigorating escape. Launch your vessel from West Windsor’s riverside areas and embark on a journey along the tranquil waters. You can also swim in secret swimming holes like the freshwater Kedron Pond, this 20ft swimming hole, and Brook Road swimming hole.

Related Events

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.

Vermont’s topography and outdoor culture make it a perfect host for other premiere endurance events throughout the year, including top gravel cycling events such as Rasputista and VT Monster produced by Streamline Events. For the multi-discipline cyclists, the state is also host to the Vermont 50 MTB organized by Ascutney Outdoors / Vermont Adaptive Ski & Sports and the epic Fox US Open of Mountain Biking, both of which are considered to be some of the Best Mountain Bike Events in New England. The Vermont Gran Fondo road cycling event, one of the Best Road Cycling Events in New England, is a stop on the Gran Fondo World Tour and a Gran Fondo National Series event. Finally, the trail runners of the group have a few great options for top tier events including the Vermont 50 Ultra Run which takes place the same day as its MTB partner event, as well as the Vermont 100 Endurance Race a Grand Slam of Ultrarunning event.