Holyoke
Trail Running Calendar near Holyoke 2026-2027
Explore the top trail runs near Holyoke for 2026-2027! We've gathered 9 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
November 2026
A 10K trail loop in Bloomfield CT on November 1, 2026, on technical single track in Penwood State Park with a three hour cutoff and proceeds supporting NAMI.
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 family friendly 5k trail run and fun walk at Chesterfield Gorge with handmade hat prizes, cookie medals and a community potluck supporting Hilltown Land Trust.
March 2027
A roughly 16 miles trail race on the Nipmuck Trail near Bigelow Hollow State Park in Union CT with technical terrain, limited aid, and a waitlist.
April 2027
Trail event in Hadley MA on April 25, 2027 with a 5K and a one mile Mushroom Mile, on-campus trails, a virtual 5K option, and proceeds to The Hartsbrook School.
June 2027
Point-to-point trail event on the New England Trail offering 112-mile and 50-mile routes to Guilford, CT, with self-supported crews and route navigation required.