Wellesley
Trail Running Calendar near Wellesley 2026-2027
Explore the top trail runs near Wellesley 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
A fall festival in Tyngsboro featuring a 3K trail race, a free kids fun run for ages 7 and under, a farmer’s market, vendors, kids activities, and food on October 25.
Community trail run from Marathon Sports Wellesley to Norumbega Reservoir with Topo Ultraventure 5 demos, sauna and cold plunge, plus coffee and breakfast.
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 half marathon and 10.5K in Upton State Forest on November 8, with limited entries, aid stations, and post race amenities.
A hilly 5K on the Melrose High School cross country course on November 8, 2026, with proceeds benefiting the Melrose XC teams.
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.
A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.
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
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.
10 mile trail race on April 10, 2027 in Andover MA along the Merrimack River with aid stations, handmade prizes, and proceeds supporting trail maintenance.