Holyoke
Trail Running Calendar near Holyoke 2026-2027
Explore the top trail runs near Holyoke for 2026-2027! We've gathered 13 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.
A fall 5K and 2 mile walk at Ashley Reservoir in Holyoke supporting Legacy Equine Center & Sanctuary with scenic water views and local wildlife.
The Village Ultra is an ultra distance running event in New Salem MA on October 11 2026, held at 23 S Main St.
A charity 5K on the scenic trails at Norbrook Farm Brewery in Colebrook CT supporting the Lymphoma Research Foundation with local beer available after the run.
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 10 km rolling loop on technical single track in Penwood State Park, organized by CT Trailmixers, with no aid stations and proceeds partly to NAMI.
A multi-distance event at Old Sturbridge Village featuring a 5K course that mixes road and trails, a scenic 2-mile walk, and a short kids trot.
March 2027
Trail race on March 28, 2027 in Union CT covering about 16 miles on the Nipmuck Trail through Yale Myers Forest with parking at Bigelow Hollow State Park.
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 in Connecticut with 112 mile and 50 mile options along the New England Trail and substantial vertical gain.