Upton
Trail Running Calendar near Upton 2026-2027
Explore the top trail runs near Upton for 2026-2027! We've gathered 22 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 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 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.
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.
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.
May 2027
A looped hill endurance event in Cumberland Rhode Island where participants run or hike as many laps as possible within a 12 hour period. The top male and female who cover the greatest distance are named King and Queen of the Hill.
June 2027
The inaugural F.I.T. 50k in Cumberland, Rhode Island is a 50k trail ultramarathon with equal parts smooth non technical and moderately technical terrain. The event includes a generous cutoff time and a $65 registration fee.