Trail Running calendar near Keene 2026-2027

The Steel Rail Races feature a marathon, half marathon, and 8K on the scenic Ashuwillticook Rail Trail in Adams, MA. Runners enjoy a technical shirt, finisher medal, and a post-race party with live music. The event supports the maintenance..

Hit the trails in Pittsfield State Forest for the Tails & Trails run, supporting local animal rescues. Choose from 50K, 25K, or 5-mile distances on a scenic course through pine woods and past boulders. Camping is available onsite for a full..

A new Soapstone Mountain Half Marathon debuts in 2026 alongside the Jerry Stage 6K. Both are trail races in Shenipsit Forest starting at Reddington Rock Riding Club, organized by the Shenipsit Striders with proceeds to trail stewardship gro..

Run a unique 4 km trail race on Cathleen Stone Island in Boston Harbor. The event includes a ferry ride to the island and concludes with a post-run party. Proceeds support free science education for Boston youth.

A lap-based trail race in Keene NH using a 12.5 km loop with options up to 50 km, technical wooded terrain, aid stations, and a cupless policy requiring personal hydration gear.

Trail races at Powisset Farm in Dover MA run through farm fields and Noanet Woodlands with four distances from 1.5 to 8.3 miles. One aid station provides water and this is a cupless race so runners must bring their own hydration carrier.

The Wildcat 5K Trail Run-Walk-Wag is a trail event on May 30, 2026, featuring separate courses for runners and walkers around Wildcat State Forest. Starting at Danvers YMCA Camp overlooking Stiles Pond, the event offers prizes, treats, and..

A scenic 2.5 mile off-road run or walk around Horn Pond paired with a festival at Ice House Park featuring food trucks, a DJ, raffles, kids activities, and over 25 local mental health and substance use providers.

A point-to-point ultramarathon on the New England Trail offering 112-mile and 50-mile options to Guilford. Entrants must make a donation to the Connecticut Forest and Parks Association and arrange their own crew and navigation.

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.

A unique trail festival centered on a rugged 3.8-mile loop featuring the infamous "staircase of death." Run solo, join a flexible relay team, or take on the casual Fun Run over a 12-hour period. Start when you like and enjoy the community a..

A two-lap mountain race at Mount Sunapee on June 7, 2026, serving as the USATF National Classic Mountain Championship and the Collegiate Mountain Running National Championships. About 9.2 miles and roughly 3,250 feet of elevation gain.

This multi-sport festival at Norbrook Farm Brewery offers trail runs, a duathlon, and mountain bike races on scenic 5K and 5-mile loops. Participants enjoy local food and a post-race brewery celebration. Registration includes a finisher med..

A trail event in Dunstable MA featuring a marked 5-mile loop with about 600 feet of elevation per loop and a 6-hour option to run multiple laps; proceeds benefit the Humane Society for Greater Nashua.

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

A trail running event at Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new 5K course entirely inside the park. Proceeds support Connecticut trail stewardship groups.

A 13.1-mile trail race in Lynn Woods Reservation on June 21, 2026, run as three 4.4-mile loops over singletrack, carriage roads and fire roads, with a focus on sustainability, safety and community engagement.

A mountain trail race at Killington Resort on June 27, 2026 covering 8.2 miles and 3,010 ft of ascent. Event features Sport Expert and Pro categories, prize awards, two aid stations and a strict summit cutoff.

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.

Notchview Ultra in Windsor MA runs multiple timed events on a 1.9 mile loop with an on-course aid station, campsite options, and beneficiaries including the Trustees of Reservations and Baypath Humane Society.