Upton
Trail Running Calendar near Upton 2026-2027
Explore the top trail runs near Upton for 2026-2027! We've gathered 28 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.
Stairs4RTroops at Gillette Stadium on October 25, 2026 is a stadium stair climb of about 5,184 steps that raises net proceeds for Homes For Our Troops.
A community fundraiser on October 25, 2026 featuring a timed 5K trail, a 1K pre-teen road race, a 5K walk, children's games and a costume contest.
Trail races at Assabet River National Wildlife Refuge in Sudbury MA with 10K, 30K and a 6-hour timed loop event on dirt and gravel double-track trails.
A continuous 50-mile trail race on a 3.1-mile loop in Wrentham, MA, with chip timing, a 12-hour cutoff, and a 75-runner field limit.
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 event in Cumberland RI on November 1, 2026 with a kids 1 mile, a 5k, a 5 mile technical trail and a 4 hour multi lap option.
Two-day Spartan Stadion weekend at Fenway Park featuring a 5 km course with 20 obstacles, kids races, and spectator options.
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 family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.
Trail races of 5.3 miles and 10 miles through Callahan State Park with road sections to and from Brophy Elementary in Framingham.
A multi terrain 5K, a scenic 2 mile walk and a kids loop at Old Sturbridge Village on November 15, 2026 with awards and participant shirts.
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 race in Cumberland, RI with kids 1 mile, 5k, 5 mile and a 4 hour multi-lap option, marked trails and chip timing.
December 2026
F.I.T.mas Trail Race in Cumberland RI offers trail distances from a kids mile to a 4 hour multi lap using a 5 mile course with chip timing and color marked routes.
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.