Ridgefield
Trail Running Calendar near Ridgefield 2026-2027
Explore the top trail runs near Ridgefield for 2026-2027! We've gathered 34 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A trail event at Ward Pound Ridge Reservation featuring a 10 km race, a November 100 km virtual challenge, rugged climbs, and fundraising for the Friends of Trailside Museum.
Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.
A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.
December 2026
March 2027
April 2027
A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.
A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.
May 2027
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 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.
June 2027
Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educational impr..