Holyoke
Trail Running Calendar near Holyoke 2026-2027
Explore the top trail runs near Holyoke for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A community fall event at Lake Wallace in Belchertown with a 5K, an accessible 1K, a Roll & Stroll, vendors, live music, and donations to the Lake Wallace Gift Account.
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 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 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.
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
Run a technical 10k loop through the rocky single track trails of Penwood State Park in Connecticut to support mental health awareness.
March 2027
A 16 mile trail race on the Nipmuck Trail in Union, CT on March 28, 2027, organized by the Shenipsit Striders with minimal aid and proceeds supporting local trail groups.
April 2027
June 2027
A point to point trail challenge across Connecticut following the New England Trail from the Massachusetts border to the Long Island Sound.