Trail Running calendar near Brattleboro 2026-2027

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

Trail race options of 50k, 30k and 10k around Edge Hill Conservation Area in Ashfield Massachusetts, run on single track and dirt roads. The event partners with Franklin Land Trust and supports habitat restoration and land conservation.

A trail race in Newport, New Hampshire on June 13, 2026 offering 6 and 3 mile routes through rocky, rooty, hilly forest trails. Proceeds support Newport Recreation and town forest trails and awards are pure New Hampshire maple syrup.

Trail races at Mansfield Hollow State Park include a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K single track loop; proceeds benefit Connecticut trail stewardship and the event is organized by the Shenipsit Striders.

A three-race summer trail series at West Hill Dam featuring well-marked wooded single and double-track trails, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

Test your physical and mental limits during this seventy two hour endurance challenge in Pittsfield Vermont. Navigate rugged forests and steep mountains while facing unpredictable tasks and grueling obstacles.

Test your limits at this three stage endurance event in Vermont featuring challenges across 4, 12, or 24 hours. Participants can progress through multiple tiers of the Hurricane Heat at the scenic Riverside Farm.

Test your endurance at Riverside Farm with a 24 hour challenge in the Green Mountains of Vermont. Complete as many 2 mile loops as possible while navigating 970 feet of elevation gain per lap.

Experience a mountain run at Killington Resort featuring 3,010 feet of vertical gain over 8.2 miles. Runners summit three peaks and tackle a steep 45 percent grade climb before finishing at the K1 base area.

Experience an obstacle course weekend at a lush Massachusetts farm featuring rolling hills and mud. Choose from 5k and 10k races or the kids division with onsite farm treats and a local brewery.

A fifteenth annual trail run in Webb Forest, Sunapee NH on June 28, 2026, covering about 4.5 miles to benefit the Sunapee Middle High School Track and Field program. The course features scenic single-track trails and a raffle of sponsor pri..

The Rochester 5K Trail Run/Walk is a 4th of July event on marked forest trails. It starts and finishes at River Brook Park, following a loop with single-track sections and rolling hills.

A run and walk along the Black River in Springfield, VT, offering 7.4K and 4K options to benefit Springfield High School Cross Country. In-person and virtual entries, packet pick-up, refreshments, prizes, and family registration pricing are..

Notchview Ultra runs July 10-13, 2026 at Notchview in Windsor, MA using a 1.9 mile loop with an aid station and bathrooms. Multiple timed and distance formats are offered, with campsite options and beneficiaries including local conservation..

Gather your team for a two day relay through the scenic Vermont countryside. Run flowy single track trails and camp under the stars at the Ascutney Outdoor Center for an unforgettable weekend of adventure.

A trail running event at Blueberry Hill Outdoor Center in Goshen, VT, offering 5 km and 10 km courses on marked trails and gravel roads, with post-race food, a raffle, awards, camping, and proceeds supporting local trail maintenance.

A technical 5.6-mile loop trail race in Northfield, NH, run over six laps with a ten-hour limit and about 4,400 feet of elevation gain; the event supports Spaulding Academy & Family Services and provides aid stations and drop bags each lap.

An annual July ultrarunning event in the southern Green Mountains offering 100 mile and 100 km courses with about 17,000 feet of climbing. The race includes a concurrent horse competition and raises funds for Vermont Adaptive Ski & Sport.