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.
August 2026
September 2026
Charity 5K run and 1.5 mile walk in Huntington MA on a mixed pavement, field and trail course that finishes at Littleville Dam.
A noncompetitive fundraising group run along the Farmington Canal Heritage Trail covering about 56 miles from West Suffield to New Haven with a 14-hour cut-off.
October 2026
Lake Wallace Fall Fest on October 3, 2026 in Belchertown offers a 5K, a 1K accessible run, a Roll & Stroll, vendors, live music, and fundraising for trail accessibility.
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.
A time-based event in New Salem MA offering 12 hour and 24 hour run or walk options around the town common on October 11, 2026.
A multi-terrain 5K, a scenic 2 Mile walk, and a short kids loop at Old Sturbridge Village on October 25, 2026, with event shirts, limited medals, and age-group prizes.
November 2026
A rolling loop trail 10K in Bloomfield CT on November 1 2026 with technical single track, a three hour cutoff, and proceeds partly to NAMI.
March 2027
A roughly 16 mile out and back trail race on the Nipmuck Trail in Union CT with minimal aid and proceeds supporting local trail stewardship.
April 2027
June 2027
Point to point trail running on the New England Trail with 112 mile and 50 mile options, requiring self support and crew assistance along a blue blazed unmarked route.