Westwood
Trail Running Calendar near Westwood 2026-2027
Explore the top trail runs near Westwood for 2026-2027! We've gathered 39 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A 5K cross-country race at Waters Farm in Sutton MA, the first stop in the USATF New England XC Grand Prix with pre-registration $35 and day of $40.
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.
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.
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
Timed trail event in Cumberland RI on a 4.2 mile loop offering 8 hour, 12 hour and 34 hour solo and team formats with distance awards and a large pit area.
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.
A 5K run and fitness walk at Highland Park in Attleboro on October 4 2026. The traffic free grass course uses two laps of a 1.55 mile loop and includes a kids 100 yard dash plus a virtual 5K option.
A community 5K and 1 mile fun run on October 11, 2026 supporting Unified programs at Beckwith and Dighton Middle Schools. Fees vary by registration period and registered runners receive T-shirts and awards for top finishers.
Six hour weighted trail race on Mansfield's WWII Veterans Memorial Trail where competitors carry chosen weight over repeated laps to score pound miles (Kz).
A harvest-season 5K trail event at White Barn Farm in Wrentham with off-road terrain, a midway water station, bib pick-up the day before, family Harvestween activities, and a portion of registrations donated to the local food pantry.
Backyard ultramarathon at Waters Farm with a 4.167 mile hourly loop, a 4.2 mile community run, a free kids fun run, and a full festival.