Trail Running Calendar Massachusetts 2026-2027

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.

Run a scenic 3-mile trail through vineyards and farms at Westport Rivers Winery. After the race, enjoy a dinner with wine and live music. All runners receive a souvenir wine glass.

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 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.

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.

The TARC Blue Hills Skyline Trail Run will take place in Canton on Saturday 11 July 2026. You can run 12 kilometers.

An 8 hour timed track event at Clapp Park on a certified 0.355 mile dirt and cinder loop, featuring chip timing, trackside bottle drop aid, age division awards, a possible virtual option, and proceeds benefitting the AYJ Fund.

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.

The Watermelon Wobbler is a 5k trail run/walk/hike through scenic conservation land and a working farm. It features a varied off-road course and supports local agriculture. On-site parking is supplemented by a satellite lot nearby.

A six hour loop ultra at Jug End State Reservation in Egremont, MA on August 22, 2026. Runners complete as many 4.2 mile laps as they wish; a 0.75 mile mini loop is available in the final hour for distance milestones.

The Old Goat Track Club XC Classic is a 5k cross-country race at Waters Farm in Sutton. It features separate men's and women's races and is the opening event for the USATF New England XC Grand Prix. Enjoy a team tent area, awards, and a pos..

The TARC Fall Classic will take place in Carlisle on Saturday 5 September 2026. You can run between 10 and 50 miles.

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

A looped trail race at Wompatuck State Park near Hingham, MA offering a 10 Miler and a 50K with mixed single track, wider trails and some paved sections. Aid stations, cupless policy, participant donations, and proceeds support charity part..

The Pumpkin Pacer 5k is a trail run, walk, or hike through scenic Wrentham conservation land and White Barn Farm. This cup-less, off-road race supports local agriculture and land preservation. It's the final event of the Farm to Trail 5K Se..

Rugged 5k trail run, ruck, or walk in Berkley MA on October 25, 2026 with in person and virtual options. Dogs may join on leash with a waiver and proceeds support The Baystate Beagle Club and Give2Those.org.

The TARC Stone Cat Trail Festival offers a classic November trail run through Willowdale State Forest. Choose from a 10K up to a 100K on a rolling, marked loop course. This community-focused event supports local trail conservation and welco..

TARC Winter Classic offers 8 32 and 40 mile trail races on the rugged Middlesex Fells Skyline Trail with roots, rocky climbs and occasional Boston skyline views. Affordable entry and proceeds support land conservation.