Westwood
Trail Running Calendar near Westwood 2026-2027
Explore the top trail runs near Westwood for 2026-2027! We've gathered 48 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A recurring in-person trail run for women and nonbinary participants on a 3 mile loop in the Fells, paced for conversation and offered on multiple dates.
In-person and virtual 5K at Lynn Woods Reservation on September 12 and 13, 2026 to benefit housing-unstable youth ages 17 to 24; $35 registration, no refunds.
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.
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
Test your endurance on a five mile trail loop in Rhode Island with 8 hour, 12 hour, and 34 hour options for individual runners and teams.
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 trail race and 5K walk through Lake Street Park trails, plus a Kid Run on the lacrosse field for age 12 and under.
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.
A 6 hour weighted trail race in Mansfield, MA where competitors carry and change weight each lap to score pound-miles called Kz on an out and back course.