Winchendon
Trail Running Calendar near Winchendon 2026-2027
Explore the top trail runs near Winchendon 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 5 mile mountain yo-yo race at Granite Gorge Mountain Park with four up and down laps, 1650 feet of elevation, benefiting the Keene Community Kitchen.
A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.
November 2026
Backyard ultra and timed 6, 12, 24 and 48 hour races near Winchendon MA on a 4.1667 mile mixed terrain loop with pompom hats for participants.
Timed loop event in New Boston NH offering 6, 12, 24 and 30 hour individual and relay formats on a 4.0 mile mostly flat loop.
Trail 5K at Temple Mountain Reservation featuring a double summit via the Wapack and Beebe Trails, one aid station, spectators welcome and no pets allowed.
May 2027
A technical trail event on the Wapack Trail in Ashburnham MA offering 21.5, 43 and 50 mile options with rugged terrain and significant climbing.
June 2027
Spartan obstacle races June 26 and 27, 2027 at a working dairy farm in Barre MA with Sprint 5 km, Super 10 km, and kids races.
August 2027
A timed single-day endurance walk on Wachusett Mountain with 7, 14, 21, or 28 mile loops, optional weighted rucks, aid stations, and venue-specific finisher gear.