Chelmsford
Trail Running Calendar near Chelmsford 2026-2027
Explore the top trail runs near Chelmsford for 2026-2027! We've gathered 36 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Cross-country races at Great Brook Farm State Park in Carlisle MA on 09/13/2026, featuring a 2K youth race and multiple 5K fields as part of the USATF New England Grand Prix.
Community trail run in Lynn MA hosted by Arc'Teryx Market Street featuring a 5k at a no drop pace on gravel roads with refreshments and a gear raffle.
A trail-based 5K run/walk and a 3K walking route at Mine Falls Park supporting Meals on Wheels of Hillsborough County, with a $30 registration and a 2026 event T-shirt for early registrants.
An 18 mile out and back trail race from Windblown Ski Area in New Ipswich NH to Watatic Mountain in Ashburnham MA with steep technical terrain and a three hour turnaround cutoff.
Trail-based 5K obstacle course at Wasserman Park with 12 or more beginner to intermediate obstacles, limited to 200 entries and a $40 fee.
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
An annual 5K cross country run or walk in Franklin Park supporting Boston Latin School Athletics. Team registration is new for 2026 and fees are tiered with free entry for BLS students.
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.