Holyoke
Trail Running Calendar near Holyoke 2026-2027
Explore the top trail runs near Holyoke for 2026-2027! We've gathered 11 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A free 8-hour trail event in Tolland, CT where runners complete as many 3-mile loops on a marked 5K-ish course as they like, with provided food and a potluck.
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 56 mile end to end run along the Farmington Canal Heritage Trail from West Suffield to New Haven raising funds for Mental Health Connecticut.
October 2026
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.
November 2026
Trail 10K in Bloomfield CT on Nov 1, 2026 honoring Kevin Hutt, run on rocky single track in Penwood State Park with proceeds partly to NAMI.
March 2027
A roughly 16 mile out and back on the Nipmuck Trail in Union CT with minimal aid stations, blue blazes, and proceeds supporting local trail stewardship.
April 2027
June 2027
Point-to-point trail runs of 112 or 50 miles along the New England Trail blue blazes to Guilford, CT, requiring dedicated crews, navigation, and night trail experience.