Chelmsford
Trail Running Calendar near Chelmsford 2026-2027
Explore the top trail runs near Chelmsford for 2026-2027! We've gathered 35 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A timed, summit-driven trail event on Wachusett Mountain offering 7, 14, 21, and 28-mile options, optional weighted vests for bonus swag, and up to 10 hours to complete the marked course.
September 2026
Trail Animals Running Club's fall trail race in Carlisle features looped courses from 10K to 50 miles, a youth fun run, marked aid stations, and a cupless policy.
Veterans Count Nashua 5K in Nashua, NH on September 5, 2026 is a community 5K with free T shirts for registrations by July 20 and free kids entries.
Trailblaze at Good Pickin’ Farm in Westford features a 5 mile trail course plus a 2.5 mile run walk and a 1K kids run with post race farm activities.
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.
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 race at Wasserman Park on September 26, 2026 featuring 12 or more beginner and intermediate obstacles and limited to 200 participants.
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.