Trail Running calendar near Chesterfield 2026-2027

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.

Experience a 5k obstacle mud run designed for unity and women empowerment at Kimball Farm in Haverhill. Join a supportive community for a day of teamwork and mud while supporting the National Breast Cancer Foundation.

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.

A 72-hour endurance race in Pittsfield Vermont on June 26-28 2026 combining physical obstacles, navigation, and mental challenges. Tickets for the Death Race require a promo code issued after acceptance by the race director.

A three-stage Hurricane Heat endurance event at Riverside Farm on June 26-27, 2026, offering 4, 12, and 24 hour tiers that together form a full 24-hour challenge; entry is 18+ with 40+ challenges and team registration options.

A 24-hour endurance challenge in Pittsfield, VT, run on repeated *2-mile* loops with 970 feet of elevation gain per loop. Participants compete for most laps or to endure the full day; tickets start at $135.

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.

A Spartan obstacle race weekend at Carter & Stevens Farm in Barre, MA, featuring a Sprint 5 km with 20 obstacles, a Super 10 km with 25 obstacles, and kids races. The farm venue includes mud, woods, rolling hills and a farm store.

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.