Trail Running calendar near Brattleboro 2026-2027

Trail races of 50k, 30k and 10k through western Massachusetts hill towns on single track and dirt roads, held in partnership with Franklin Land Trust and featuring aid stations, first aid and locally produced awards.

A trail race in Newport, New Hampshire featuring 6 miles and 3 miles on rocky, rooty, hilly town forest trails; age and gender categories award Pure NH maple syrup to top three finishers and proceeds support local trails.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13, 2026, with routes on single track trails and carriage roads. Proceeds support Mass Audubon conservation; water stations, finish area refreshments, and limited parking.

A community 5K at Hampshire Regional High School combining paved roads and technical wooded trails, plus a one mile fun run around campus; post race refreshments and awards are provided.

Trail races at Mansfield Hollow State Park: a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K trail loop. Proceeds support Connecticut trail stewardship groups.

A community run on a three-loop course at the Natick Community Organic Farm, mixing trail, field, and road surfaces. Participants receive a commemorative chicken medal and top finishers are tracked in adult and kid categories.

A 5.6 K trail run and walk at Berry Pond in Harold Parker State Forest on June 14, 2026. Walkers and leashed dogs are welcome; prizes are awarded, all entrants receive a bandana, and hotdogs are provided after the race.

A loop trail run at Lawson Lake Park on June 20, 2026, featuring a 1.25 mile course with lake and creek views. Options include 2.5M, 5M, a one-hour format, and team entries; awards and a meal ticket are included.

Part of the Grit Series at Dublin Outdoor Center, this trail event offers a 10K and a half marathon over rugged trails with significant elevation gain and views of Mount Monadnock. Registration runs May 3 to June 6, 2026.

A 5K through Camp Jewell’s roads and wooded trails including a covered bridge, plus a free one mile kids run. Pre entry is $30 before June 6 and increases to $35 afterward.

A loop-format trail event in Adams, MA where runners choose one, two, or three loops on machine and hand-built singletrack. Proceeds support Thunderbolt Ski Runners' stewardship of trails around Greylock Glen and Mount Greylock.

Five Monday evening 5K trail races at Town of Wilton Camp Saratoga across June to August 2026. Entries available per race or as a series package; proceeds benefit the Wilton Wildlife Preserve & Park.

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 event in Pittsfield, Vermont on June 27 to 28, 2026. Runners repeat a two mile loop with 970 feet of elevation gain as they compete for most laps or aim to last the full 24 hours.

A single 8.2 mile trail race at Killington Resort on June 27, 2026 with 3,010 feet of elevation gain and three summit climbs. The field is capped at 700 runners and includes aid stations, race swag and professional photos.

A Spartan obstacle weekend at Carter and Stevens Farm in Barre, MA on June 27 and 28, 2026 with Sprint, Super, and kids races, plus an obstacle workshop and spectator access.

A charity team challenge on June 27, 2026 in Bristol, NH that recreates Special Forces mission tasks. Teams of 6–12 choose Operator or Recruit levels, with awards for top teams, MVPs, fundraising leaders, and participant milestones.

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..