Wilton
Trail Running Calendar near Wilton 2026-2027
Explore the top trail runs near Wilton for 2026-2027! We've gathered 32 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A forested 5K on August 9, 2026 at Bridgewater Town Park featuring new trails, modest hills, participation gifts, and prizes for top finishers.
Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.
On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are collected.
September 2026
An obstacle-based 5K at Short Beach, Stratford on September 12, 2026, with 18+ obstacles and fundraising for the Sterling Community Center.
Timed trail races in Pawling NY offering 24, 12, 6 and 3 hour options on an approximately 1.68 mile loop with on course aid and athlete camping.
A USATF-sanctioned trail event in Upper Nyack with a 50 mile option featuring four 11.5 mile loops, about 9,700 feet gain, and three aid stations.
Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.
October 2026
A 30-hour trail ultra at Roosevelt Forest in Stratford CT with 2.5-mile loops, buckles at 100 miles, and a 50 participant field limit.
A 4-mile trail race through Irvington Woods on October 4, 2026, starting and finishing at the Irvington High School campus; rain or shine.
A scenic 5K through the carriage roads of Rockefeller State Park Preserve with hilly terrain, Swan Lake views, awards, t shirts and proceeds supporting carriage road maintenance.
A single-loop trail half marathon through five parks in lower Westchester County, New Rochelle. Most of the course is on dirt and wooded trails and passes through areas with visible wildlife.
A scenic 5K trail run and walk at Blydenburgh County Park on October 11, 2026 with in-person and virtual options. Participants receive a race tee, on course hydration and age group recognition while proceeds benefit a local running foundation.
A trail event at Muscoot Farm on October 25, 2026: a five-mile race plus two kids races, kids medals, and Farm Bucks for finishers.
November 2026
Timed trail event at Gurski Farm in Brookfield CT featuring an 8 hour race, a 4 hour option, and a 5K canicross on a 4 mile loop.
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.