Trail Running calendar near Middlebury 2025-2026

The Bloodroot Ultra will take place in Pittsfield from Wednesday 7 May 2025 to Saturday 10 May 2025. You can run between 10 and 200 miles.

Infinitus is an extraordinary endurance event hosted by The Endurance Society, taking place from May 15 to May 25, 2025, in Ripton, Vermont. Participants can choose from a variety of challenging race options, including distances ranging from 9 miles to an impressive 888 kilometers. The event is set..

The Black Fly Trail Run, taking place in Westmore, Vermont, offers a unique running experience with options for a half marathon, 10-miler, and 5K. This annual event features stunning terrain, including dirt roads and private trails, providing a challenging yet rewarding atmosphere for runners of all..

The Sunapee Scramble is a challenging mountain running event taking place in Sunapee, New Hampshire, on June 1, 2025. This race will serve as the USATF National Classic Mountain Championship and the sole selection race for the 2025 US Classic Up/Down Mountain Running Team, which will compete in Spai..

The Cirque Series - Cannon Mountain is an exciting running event set in Franconia, New Hampshire, featuring a challenging 6.7-mile course with an elevation gain of 3,386 feet. Participants can choose from three divisions: Sport (beginner/intermediate), Expert, and Pro, catering to various skill leve..

The Race to the Top of Bradford is an exciting running event taking place in Bradford, Vermont, featuring a challenging 5K race that ascends 850 feet to the summit of Wright's Mountain. Participants will enjoy scenic trails and breathtaking views before looping back to the start. Additionally, a 1.5..

The Catamount Ultra is a trail running event held at the scenic Trapp Family Lodge in Stowe, Vermont. Participants can choose between two distances: a 25k and a 50k race. The 25k course features wide, hard-packed dirt trails that meander through beautiful highland pastures and hardwood forests, whil..

The Cirque Series - Killington is an exciting running event set to take place in Killington, Vermont. This inaugural race features a challenging 7.2-mile course with an impressive elevation gain of 3,133 feet, summiting three of the resort's six peaks. Participants can choose from three divisions: S..

The Harry Corrow Freedom Run is a celebratory running event held on July Fourth, offering participants the choice of distances ranging from 2 miles to a Half Marathon (13.1 miles). The run takes place on a scenic gravel bike path and wooded trails, coinciding with the July Fourth festivities in Newp..

The F.I.T. Sun Mountain Challenge is an exciting running event taking place at Bromley Mountain in Peru, Vermont. Scheduled for July 5, 2025, the challenge features three race options: a 5K, 10K, and a 25K ultra, catering to participants of all skill levels.Runners will enjoy stunning mountain views..

The Goshen Gallop is an annual running event held at the Blueberry Hill Outdoor Center in Goshen, Vermont, featuring 10K and 5K trail races. Celebrating its 47th year, the event emphasizes fun, community, and the enjoyment of nature, with proceeds supporting the maintenance of the trails used during..

The Whiteface Mountain Races, organized by Red Newt Racing, is a challenging running event set in the stunning Adirondack Mountains. Participants can choose from various race options, including a 10K and a 21K loop race, both featuring significant elevation gains and losses. The event is known for i..

The Loon Mountain Race is a challenging mountain trail race that spans 6.03 miles, culminating at the summit of Loon Mountain in Lincoln, New Hampshire. Known for its steep inclines, the course features a significant elevation gain of over 3,000 feet, with sections reaching a daunting 40% grade. Thi..

The Vermont 100 Endurance Race is a premier ultramarathon event held annually in July, attracting endurance athletes from around the globe. This challenging race features a 100-mile course that includes 17,000 feet of elevation gain, winding through scenic country roads and forested trails in the so..

The Wakely Dam Ultra is a challenging 55K ultra marathon set in the scenic Adirondack Park of New York State. The race takes place along a remote section of the Northville Placid Trail, featuring a total elevation gain of 3300 feet. Participants must be self-supported, providing their own aid throug..

The Moosalamoo Ultra is a popular trail running event held in Goshen, Vermont, starting and ending at the scenic Blueberry Hill Inn. This race features two challenging distances: a 14-mile and a 36-mile course, both offering stunning views and rugged mountain trails within the Moosalamoo National Re..

The Barre Heritage Trail 5K is an annual running event organized by Central Vermont Runners, taking place during the Barre Heritage Festival. This race offers participants a scenic route through the beautiful trails of Barre, promoting health and community engagement. The event is designed for runne..

The Ragged 75 Stage Race and 50K is an exciting running event taking place from August 1 to 3, 2025, in Danbury, NH. The stage race covers a challenging 75 miles with approximately 15,500 feet of elevation gain, featuring technical single-track trails and steep climbs. Participants can also opt for..

The Slate Valley Scramble, organized by Slate Valley Trails, is a trail running event taking place on August 9, 2025. Participants can choose between an 8k and a half marathon, both set on scenic singletrack and double-track trails in Vermont's Slate Valley. A Kid's Fun Run is also available for chi..

The Delta Dental Race To The Top Of Vermont is an annual event held every August, attracting hikers, bikers, and runners from across the U.S. and Canada to conquer Mt. Mansfield, the highest peak in Vermont.The challenging 4.3-mile course ascends the historic Mansfield Toll Road, featuring a steep e..