Westwood
Trail Running Calendar near Westwood 2026-2027
Explore the top trail runs near Westwood for 2026-2027! We've gathered 27 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
An annual festival at Brigham Hill Community Farm combining a community 5K and kids fun run with vendors, food, apple tastings, hayrides, and family activities.
Trail races in Cumberland, RI offering a Kids 1 Mile, a 5K, a 5 Mile and a four hour multi-lap option with chip timing and marked courses.
Two-day Spartan Stadion weekend at Fenway Park featuring a 5 km course with 20 obstacles, kids races, and spectator options.
Trail running at Wompatuck State Park with a 4 mile loop and three formats: a single loop, an 8 hour loop challenge, or a Backyard style option.
Trail races in Upton State Forest offering a 10.5K and a two-lap half marathon over technical, hilly single-track and forest roads with limited fields.
A hilly 5K at Pine Banks Park in Melrose supporting Melrose High School cross country teams, with overall and age group awards and post race refreshments.
A six hour timed trail race on a rocky 5K loop at Wright Locke Farm with a cupless aid station, goat companions, a $35 entry, and limited registration.
A community trail event at Good Pickin’ Farm with a scenic 5 mile run, a 2.5 mile walk or run, and a 1K kids run plus post race farm activities.
Trail races of 5.3 miles and 10 miles through Callahan State Park with road sections to and from Brophy Elementary in Framingham.
A scenic 5K trail run in Wrentham, MA on November 26, 2026 with awards, post-race donuts and cider, a raffle, and a $25 registration fee.
Trail trail races in Cumberland RI on Nov 28, 2026 with a kids 1 mile, 5k, 5 mile and a 4 hour multi lap option using chip timing.
December 2026
Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.
Trail event in Cumberland, RI offering kids 1 mile, 5K, 5 mile and a 4 hour multi lap with chip timing and marked courses.
January 2027
Winter trail event at Hale Education in Westwood MA offering a 30 hour race and a 15 mile looped course with marked trails, cupless aid stations, and required cold weather gear.
March 2027
Trail races at Monastery Trails in Cumberland, RI on March 14, 2027 offer distances from a 1 mile kids run to a 100K 12 hour ultra. Team ultra entries and a multilap 5 hour option are available and all finishers receive a medal.
Trail Animals Running Club hosts 6 hour and 3.5 mile loop trail events at Hale Reservation in Westwood, MA with marked trails, cupless aid, and limited parking.
April 2027
An obstacle course race in Cumberland, Rhode Island featuring a 3.2 miles course with about 1,000 feet elevation, multiple wave formats including elite and age group competition, multilap sessions, and a 12 hours ultra option.