Darien
Trail Running Calendar near Darien 2026-2027
Explore the top trail runs near Darien for 2026-2027! We've gathered 56 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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.
A fall cross country 5K in Van Cortlandt Park with race day packet pickup, age group awards, live results and a pair of translucent rainbow sunglasses for each participant.
Six hour running and relay event at Belmont Lake State Park on September 27, 2026 where individuals and teams compete for the most distance on a 2.50 mile loop.
A scenic 3.1 mile road and trail run through the New York Botanical Garden with a stretch in the Thain Family Forest and post-run festivities on Daffodil Hill.
A scored NYRR cross country race at Van Cortlandt Park featuring a 5K course as the first event in a three-race fall series, with youth programming via Rising NYRR.
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.
Scored cross country 5K at Van Cortlandt Park in the Bronx, part of an NYRR series that includes youth races, accessibility provisions, and official results via the NYRR app.
Four-day trail event in Rocky Point, NY featuring a 10.48-mile Pine Barrens loop with eight distance options from 10 miles to 150 miles.
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.
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.
Trail 5K at Blydenburgh County Park on October 11, 2026 offering in person and virtual options, participant tees, refreshments, and age group recognition.
Multi day running weekend in Bay Shore, NY with marathon, half marathon, 10K, 5K, kids 1K, relay and a virtual 26.2 miles challenge.
Outrun the Stigma 5K Run/Walk in Massapequa Park NY features a 3.1 mile mixed surface course, kids fun run, and finisher medals for adult 5K finishers.
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.