Westwood
Trail Running Calendar near Westwood 2026-2027
Explore the top trail runs near Westwood for 2026-2027! We've gathered 45 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail ultra in Cumberland Rhode Island on Oct 3 and 4 2026 featuring a 5 mile loop and 34, 12, and 8 hour individual and team formats.
A community cross-country 5K at Franklin Park on October 3, 2026, open to Boston Latin School affiliates and local runners and walkers with team options and tiered fees.
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.
A park-based, traffic-free 5K in Highland Park, Attleboro with a grass loop course, a kids 100 yard fun run, on-site activities, awards, and a virtual 5K option.
Community 5 mile trail run at Lynn Woods Reservation with a no drop pace, Norvan trail vest demos, post-run refreshments, and free parking.
A 5K and 1 Mile Fun Run at the Dighton Rehoboth High School cross country course raising funds for student Unified programs, with early registration and event awards.
10 km trail race in Milton MA on 10/11/2026 featuring a moderately technical, low elevation course; registration runs 9/25 to 10/11, fee $20.
A six hour weighted trail race in Mansfield MA where competitors carry and adjust weight each lap and score by pound miles called 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.
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 rugged 5k trail run, ruck, and walk in Berkley MA on October 25, 2026 that honors military and first responder K9 teams while supporting local charities.
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 stadium stair-climb at Gillette Stadium raising funds for Homes For Our Troops, covering about 5,184 steps in the lower bowl with individual, team, and fundraising options.