Shirley
Trail Running Calendar near Shirley 2026-2027
Explore the top trail runs near Shirley for 2026-2027! We've gathered 31 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Trail 5K obstacle course at Wasserman Park with 12+ beginner to intermediate obstacles, limited to 200 entrants, including a race shirt, finisher medal, and a Spartan entry for early registrants.
Backyard Ultra in Leominster State Forest on September 26, 2026; runners repeat a 4.167 mile loop each hour until only one remains.
Trail races and a 6 hour timed event through Assabet River National Wildlife Refuge with aid stations, cupless rules, pacer options, and proceeds supporting refuge projects.
October 2026
A 5K trail race and 5K walk through Lake Street Park trails, plus a Kid Run on the lacrosse field for age 12 and under.
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 with snacks.
Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.
A multi format trail event on the Granite Town Rail Trail in Brookline and Milford NH on October 17 and 18 2026, featuring 7.5 mile relays, 15 mile and 30 mile races and a 30 hour ultramarathon. Proceeds support local trail conservation.
A backyard ultramarathon at Waters Farm with a one loop hourly race, a 4.2 mile community run, a free kids fun run, and a full festival day.
A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.
A fall festival in Tyngsboro featuring a 3K trail race, a free kids fun run for ages 7 and under, a farmer’s market, vendors, kids activities, and food on October 25.
Community trail run from Marathon Sports Wellesley to Norumbega Reservoir with Topo Ultraventure 5 demos, sauna and cold plunge, plus coffee and breakfast.
November 2026
A backyard ultra weekend at Kenty’s Farm with a 4.16667 mile loop, Last Runner Standing format, and timed 6/12/24/48-hour events plus themed community hours.
Trail 5K at Temple Mountain Reservation featuring a double summit via the Wapack and Beebe Trails, one aid station, spectators welcome and no pets allowed.
Trail half marathon and 10.5K in Upton State Forest on November 8, with limited entries, aid stations, and post race amenities.