Trail Running calendar near Pittsfield 2025-2026

We have found 44 Trailruns within 80 miles of Pittsfield. See below where and when you can find the races.

The The Mucker will take place in Montpelier on Sunday 27 April 2025. You can run between 5 and 5 miles.

The 45th Annual Doc Lopez Run for Health is set to take place in Elizabethtown, NY, featuring a half marathon and a 5K trail run. This event aims to benefit the University of Vermont Health Network - Elizabethtown Community Hospital. Participants can enjoy scenic views along the challenging half mar..

May 2025

The White Lake Ultras is an annual endurance running event held at White Lake State Park in Tamworth, NH. Participants can choose to run for 6, 12, or 24 hours on a slightly technical 2-mile single track loop that features scenic views of the lake and surrounding forest. The event promotes sustainab..

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.

The Ralph Waldo Emerson Trail Race is a unique running event held in Concord, NH, designed to benefit the Ralph Waldo Emerson School for Preschoolers. Participants can choose between two race distances: a short course of approximately 3.9 miles and a long course of about 7.0 miles. The race takes pl..

Infinitus is an extraordinary endurance event organized by The Endurance Society, taking place from May 15 to May 25, 2025, in Ripton, Vermont. Participants can choose from a variety of challenging distances, including 9 miles, marathons, and even the extreme 888k, which spans 551 miles. The event i..

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 17 May 2025. You can run between 5 and 5 kilometers.

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, now in its fourth year, features stunning terrain, including dirt roads and private trails, providing a challenging yet inspiring atmo..

The Mayfly Ultra is an exciting running event taking place in Stony Creek, NY, featuring a challenging 49K ultra marathon and a 27K mini run, along with a relay option for teams of four. Set against the stunning backdrop of the Adirondack Park, participants will navigate both paved and unpaved roads..

The Fitzwilliam to Troy Depot Day Cheshire Rail Trail Fun Run is a 5-mile running event taking place along the scenic Cheshire Rail Trail, starting from the original Fitzwilliam Railroad Depot to the newly restored Troy Depot. This event celebrates the historical significance of the rail trail, whic..

June 2025

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 taking place in Franconia, New Hampshire. This inaugural race features a challenging 6.7-mile course with an impressive elevation gain of 3,386 feet, starting at the Peabody Base Area and culminating at the summit of Cannon Mountain. P..

The Drummer Hill Trail Races, set in Keene, NH, offers a unique trail running experience with multiple distance options: 50K, 37.5K, 25K, and 12.5K. Participants can choose how many 12.5K laps to complete, allowing for a customizable challenge. The course features a mix of technical single track and..

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 wind through beautiful highland pastures and hardwood forests, while t..

The Cirque Series - Killington is an exciting running event set to take place in Killington, Vermont, featuring a challenging 7.2-mile course with an elevation gain of 3,133 feet. Participants can choose from three divisions: Sport (beginner/intermediate), Expert, and Pro, catering to various skill..

July 2025

The Ordination Rock Run is a family-friendly 5k fun run held annually on July 4th in Tamworth, New Hampshire, as part of the town's Independence Day celebrations. This event celebrates the historical significance of Ordination Rock, where Samuel Hidden was ordained in 1792. Participants enjoy a scen..

The F.I.T. Sun Mountain Challenge, taking place in Peru, Vermont, offers a thrilling experience for runners of all levels with events including a 5K, 10K, and a 25K ultra challenge. Set against the stunning backdrop of Bromley Mountain, participants can enjoy beautiful trails and breathtaking mounta..

The Goshen Gallop is an annual running event held at the Blueberry Hill Outdoor Center in Goshen, Vermont. Celebrating its 47th year, the event features both 10K and 5K trail races that traverse scenic gravel roads and cross-country ski trails within the Moosalamoo National Recreation Area. Particip..

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..