Westwood
Trail Running Calendar near Westwood 2026-2027
Explore the top trail runs near Westwood for 2026-2027! We've gathered 44 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
November 2026
Obstacle course weekend at Fenway Park in Boston on Nov 7 and 8 2026 featuring a 5 km Stadion with 20 obstacles and kids races.
Trail event at Wompatuck State Park with a single 4 mile loop, an open 8 hour multi loop format, and a non eliminative Backyard style option.
Trail races in Upton State Forest offer 10.5K and half marathon options over technical, hilly single track and forest roads. The event has a 250 runner cap and aid stations spaced roughly every three miles.
Six-hour timed trail race on a 5K loop at Wright Locke Farm in Winchester MA with rocky rollers, a cupless barn aid station, and a youth discount.
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.
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.
February 2027
Winter trail event at Hale Education in Westwood, MA offering 15 mile and 30 hour looped courses with marked trails, cupless aid stations, and strict cold-weather gear rules.
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.
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.
Trail Animals Running Club hosts looped trail races at Jericho Town Forest with 10K, half marathon, marathon and 50K options, a single aid station, and strict time cutoffs.