Trail Running calendar near Chesterfield 2025-2026

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.

IronHike Series Spring 26 takes place June 4 to 7 at Mohawk Mountain, CT, with solo and team endurance options from 15 to 152 miles. This non competitive FlexRelay invites crews to self manage pacing, rest and night trekking.

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.

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..

Manitou’s Revenge is a rugged 53 mile ultramarathon through the Catskill Mountains on June 20, 2026, featuring roughly 15,000 ft of climbing and technical, often remote terrain. Expect limited aid and a true test of endurance and trail skil..

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 Soapstone Assault is a rugged 5.5 mile trail race in Somers, CT with six climbs and about 1,500 feet of ascent. Limited to 50 runners, it is a tough course for experienced runners and includes a pre race safety briefing and breakfast.

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.

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 Triple Dam 10K in Perkinsville VT on August 23, 2026 for a scenic road and trail loop with a fun calf deep river crossing. Open to runners and walkers, proceeds support Springfield High School cross country.

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.

Trail Animals Running Club Fall Classic at Great Brook Farm State Park offers scenic trails and distances from 10K to 50 mile, plus a youth fun run and Mischief Mile. Aid stations and vegan options support runners in this cupless event.

Tackle the Shawangunk Ridge Trail near Rosendale NY for sweeping Hudson Valley views across cliffs, sky lakes and rocky ridgelines. Choose 70 Miler, 30 Miler or half marathon for a rugged, self supported navigation challenge.

Macedonia Trail Race at Macedonia Brook State Park offers scenic single track and forest trails with climbs and viewpoints. Choose 50K, 25K or 12K for a rewarding day of trail running in Connecticut.

The Vermont 50 is a classic late September mountain bike and ultra run at Mount Ascutney offering 50 mile and 50K options, plus family fun and kids activities on Saturday. Proceeds support Vermont Adaptive Ski and Sports.

Run the newly restored Moosup Valley State Park Trail in Moosup CT with 5K, 10K and a kids fun run on Sunday September 27, 2026. Postrace medallions or tee shirts, food and drink, leashed dogs welcome, and proceeds benefit the Rotary Club o..

Tackle an Everesting relay across 61+ miles and 29,029 feet of climbing at Mohawk Mountain in Cornwall CT, with a 72 hour window to run, hike or walk. Team up and test endurance on this epic fall challenge.