Trail Running calendar near Milton 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 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 well-maintained dirt trails that wind through beautiful highland pastures and hardwood forests, while the..

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 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 mountain race, both featuring significant elevation gain and loss. The event also includes..

The Vermont 100 Endurance Race is a prestigious ultramarathon that challenges athletes with a 100-mile course featuring 17,000 feet of elevation gain. Taking place in the scenic southern Green Mountains, the race combines rugged country roads and forested trails, attracting participants from around..

The Barre Heritage Trail 5K is an annual running event organized by Central Vermont Runners, taking place in Barre, Vermont. This trail race is designed for participants of all skill levels, promoting community engagement and healthy lifestyles. The event showcases the scenic beauty of the area whil..

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 showcasing the stunning landscapes of the Moosalamoo National Recreation Area. Parti..

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..

XTERRA Bromont is an exciting off-road sports event scheduled for August 23-24, 2025, at the Bromont Olympic Equestrian Park and Lake Bromont beach in Canada. As part of the XTERRA World Tour, it features a variety of races, including off-road triathlons and trail runs, catering to participants of a..

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..

The Groton Forest Trail Run features a marathon, 25K, and 10K trail running events, set in the scenic Boulder Beach State Park in Groton, Vermont. This annual event attracts runners of all levels, offering a chance to experience the beauty of the forested trails. The next scheduled run will take pla..

The Kilkenny Ridge Race, taking place in Stark, New Hampshire, features a challenging course that follows the Kilkenny Ridge Trail. Participants can choose from three distances: 50 miles, 25 miles, and 25K, each offering significant elevation gains and rugged terrain. The race is designed for experi..

The Devil's Den Ultra is an exciting running event taking place in Bradford, Vermont, featuring a challenging 6.4-mile loop course on Wright's Mountain. Participants can choose from three race lengths: a 30-hour, a 12-hour, or a 6-mile race. The course offers a mix of terrain, including steep climbs..

The Trapp Lodge Mountain Marathon is a challenging trail running event held in the picturesque Green Mountains of Vermont, specifically at the Trapp Family Lodge. Participants can choose between a half marathon and a full marathon, both of which feature a mix of winding single track and rugged dirt..