Cheshire
Trail Running Calendar near Cheshire 2026-2027
Explore the top trail runs near Cheshire for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
April 2027
Timed trail races at Deer Lake Outdoor Center in Killingworth CT include a roughly 5 mile course with about 500 ft of elevation gain and a new timed 1 mile kids run.
May 2027
Twelve hour trail endurance run on a scenic 5K loop at Chatfield Hollow State Park with individual and relay options and a 100 runner limit.
A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.
A Last Person Standing trail race on Ragged Mountain in Berlin, CT using repeat one-hour 3.11-mile loops until one runner remains; field limited to 55.
June 2027
A 5K trail and obstacle run on the 400-acre Gaylord Specialty Healthcare campus in Wallingford, CT supporting adaptive sports and hospital fundraising.