Wilton
Trail Running Calendar near Wilton 2026-2027
Explore the top trail runs near Wilton 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.
September 2026
Test your endurance at the Pawling 24 Hour Trail Running Festival featuring multiple timed races on a scenic 1.68 mile loop in Lakeside Park.
Experience a challenging 50 mile or marathon trail race featuring 9600 feet of elevation gain and scenic Hudson River views at Hook Mountain.
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 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.
Four miles of trail running through the Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus on October 4, 2026.
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.
Scenic 5K at Rockefeller State Park Preserve featuring hilly carriage roads, age group and team awards, t shirts and refreshments, with proceeds supporting carriage road maintenance.
A trail half marathon in New Rochelle that loops through five Westchester County parks and runs mostly on dirt trails shaded by woodland canopy.
Trail 5K at Blydenburgh County Park on October 11, 2026 offering in person and virtual options, participant tees, refreshments, and age group recognition.
Trail event at Muscoot Farm in Katonah on October 25, 2026 featuring a 5 mile race and two kids races, with Farm Bucks and kids medals.
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.
Trail events at Ward Pound Ridge Reservation: a 10k trail race on November 8, 2026 and a month long Raven 100k Challenge with wooden finisher medallions.
Backyard Ultra at Cranbury Park in Norwalk, CT where runners repeat a precise 4.167 mile loop every hour until only one runner 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.