Wilton
Trail Running Calendar near Wilton 2026-2027
Explore the top trail runs near Wilton for 2026-2027! We've gathered 35 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 30 hour loop ultrarun in Roosevelt Forest CT on 2.5 mile laps offering distances to 100 miles with a finisher buckle and a single pavilion aid station.
A 4 miles trail race through Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus.
A 5K trail run and an accessible short run/walk on private Gemstone Farm in Wilton, CT on 10/10/2026, with farm access, post-event food and entertainment, supporting The Prospector.
A scenic October 5K on the carriage roads of Rockefeller State Park Preserve with hilly terrain, awards, and proceeds supporting carriage road maintenance.
Trail half marathon in New Rochelle running a single loop through five Westchester parks on mostly dirt shaded trails with frequent wildlife on October 11, 2026.
A scenic trail 5K at Blydenburgh County Park on October 11, 2026 with in-person and virtual options, race tee, refreshments, and age-group recognition.
Trail running at Muscoot Farm with a 5 mile race and two kids races on October 25, 2026 in Katonah, NY.
November 2026
Experience a community-focused trail race featuring a 4 mile loop of rolling farm trails and single track with timed options, a 4 mile distance, and a 5K Canicross.
A 4K grass cross country event at the Northport VA Golf Course with military and youth categories, a short fun run, awards, and proceeds supporting local veterans.
A trail 10k at Ward Pound Ridge Reservation on November 8, 2026 plus a monthlong November Raven 100k Challenge with a wooden finisher medallion.
Inaugural Great Lawn Backyard Ultra at Cranbury Park asks runners to repeat a 4.167 mile loop each hour until one person remains.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.
A farm based 5K trail run plus a kids fun run for ages 6 and under in Yorktown Heights supporting Friends of Hilltop Hanover Farm.
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.
Somers Thanksgiving Turkey Trot in Somers, NY features a 5K trail race and a 1 Mile fun run with age-group awards, shirts, medals, and packet pickup.
A community Thanksgiving run at Darien High School featuring a 5K and 1-mile walk/run, with music, food, and proceeds benefiting The Depot youth center.
December 2026
A backyard ultra at Blydenburgh County Park: runners repeat a 4.167 mile loop each hour until one completes the final loop; proceeds support Long Island trail maintenance.