Trail Running calendar near Upton 2026-2027

The Grills Trail Run will take place in Westerly on Saturday 24 October 2026. You can run between 10 and 10 miles.

The Pumpkin Pacer 5k will take place in Wrentham on Saturday 24 October 2026. You can run 5 kilometers.

A mountain race in Keene, NH featuring four repeated climbs and descents on mostly ski trails and some single-track, totaling 4.9 miles and 1650 feet of elevation. Proceeds support the Keene Community Kitchen and prizes are awarded.

Rugged 5k trail run, ruck, or walk in Berkley MA on October 25, 2026 with in person and virtual options. Dogs may join on leash with a waiver and proceeds support The Baystate Beagle Club and Give2Those.org.

TARC Stone Cat Trail Festival in Willowdale State Forest (Ipswich, MA) offers looped trail distances from 10K to 100K, a Cider Donut Mile and a free youth fun run, with proceeds supporting local land stewardship.

Enjoy scenic trails around Watchaug Pond at the Li'l Rhody Runaround on November 15, 2026, with 8 mile and 4 mile course options. Part of the WTAC Fall Trail Race Series, it welcomes runners of all levels.

TARC Winter Classic in Stoneham offers 8, 32 and 40 mile trail races on the white blazed Skyline Trail with rugged roots, rocks, frequent climbs and Boston skyline views. Expect technical trails, minimal markings and a festive finish.