Trail Running calendar near Union 2025-2026

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

Explore trails around Soapstone Mountain and Shenipsit Forest at the Soapstone Mountain Trail Races in Stafford Springs, CT on May 17, 2026. Pick a half marathon or 6K, support local trail stewardship, and register January 1, 2026.

Take on the Drummer Hill Trail Races in Keene NH on May 23, with a 12.5k loop you can repeat for 12.5K, 25K, 37.5K or 50K. Expect technical single track, rocks, roots and stream crossings, aid stops and DHTR drumstick awards.

Run the Mine Hill half marathon on 24 May 2026 in Roxbury Connecticut, starting and finishing at Mine Hill Distillery. Enjoy rolling country roads with sweeping farm views, then celebrate at the distillery after party.

Hit the trails at the Wildcat 5K Trail Run Walk Wag in Boxford on May 30, 2026, for a scenic 5K through Wildcat State Forest with pond views and separate courses for runners and walkers. Enjoy post race treats, swag, and prizes for top fini..

IronHike Spring 26 at Mohawk Mountain CT in June offers endurance routes from 15 to 152 miles for solo runners, teams and families in a flexible relay format. Enjoy basecamp camping, support stations and finisher gear.

Run a scenic 5 mile Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on Saturday, June 6, 2026. Enjoy family fun, food, and festivities while supporting the Fitzwilliam and Troy historical societies.

Run a scenic 3 mile trail through farm fields and finish among the vineyard rows at Westport Rivers Vineyard and Winery. Celebrate after with wine, music, BBQ and a souvenir glass for a festive postrun party.

Join the Run in the Park 5K at Eisenhower Park in Milford on June 7 to support the Milford Rotary and the Beth El Center. Enjoy a scenic, mostly flat trail loop welcoming runners, walkers, hikers, families, dogs, and teams.

Explore rugged singletrack and an old railroad bed on a tough 5 mile loop at the Flat Rock Trail Race in Dunstable MA. Proceeds benefit the Humane Society for Greater Nashua and runners can repeat loops for up to six hours.

Run the scenic 15.7 mile Nipmuck South Trail at Mansfield Hollow State Park, following the Nipmuck Trail along the Fenton River through woods, fields and a climb to a cliff. Proceeds benefit Connecticut trail stewardship groups and the Blue..

Notchview Ultra invites runners July 10 to 13, 2026 in Windsor, MA, offering formats from 100.7 miles down to 6 hour on a scenic 1.9 mile loop. Enjoy frequent aid, camping, swag, and proceeds supporting local conservation.

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

Soapstone Assault is a rugged 5.5 mile trail race with six steep climbs and about 1500 feet of climbing. Field limited to 50 runners and parking is tight, making this an intimate but fierce challenge with post race breakfast sandwiches.

Join the Sweltering Summer Ultra, an 8 hour track challenge at Clapp Park in Pittsfield where runners and walkers lap a cinder loop and hit a marathon split. Chip timing, live leaderboard, refreshments and awards support the AYJ Fund.

Experience the Stonington Cross Country 5K at Stonington High School, a scenic route from the track through campus streets and wooded trails to a field finish. Family friendly with a kids half mile for ages 10 and under.

Join an 8 hour trail gathering at Crandall's Park and run as many 5K loops as you like. Potluck, raffles, prizes and a Shenipsit Striders 50th anniversary gift for those who complete at least one loop.

Run the Jug End Loop Ultra on August 22, 2026 at Jug End State Reservation in Egremont MA, a six hour timed event on a scenic, hilly 4.2 mile loop through woods and an apple orchard. Rack up laps, earn a handmade mug and support local chari..

Run the Old Goat Track Club XC Classic at Waters Farm in Sutton, a spike friendly 5K cross country loop and USATF New England Grand Prix stop. Perfect for teams and individual racers, with finish line snacks and a nearby after party.

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