Trail Running calendar near Darien 2026-2027

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.

A multi-day trail festival at Wawayanda State Park in mid-September 2026 featuring races from 1 mile to 100 miles, free participant camping, a 36 hour 100 mile option with a single late cutoff, and community mental health partnerships.

The Hook Mountain Ultra is a demanding 50-mile or 27-mile trail race in Upper Nyack, NY. The course features repeated loops with significant climbs, ridge running, and scenic Hudson River views. It includes full aid station support and has..

The Where the Pavement Ends trail race offers a technical 4.25-mile single loop or an 8-mile double loop through the Hemlock Hills. It's part of the multi-race Trail Mix Series. Both races start and finish at the Lake Windwing ballfields in..

Run a scenic 5K trail race through 300 acres of natural terrain at Winding Trails in Farmington. Compete for age group awards and the local Lee Chisholm Award on a course surrounding Walton Pond.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

The Caldwell Cougar Chase 5K and 8K will take place in Woodland Park on Friday 25 September 2026. You can run between 5 and 8 kilometers.

Trail races on the McDade Trail through the Delaware Water Gap on September 26, 2026. Distances are 50K and 25K with post-race food, a finishers item, and a portion of fees donated to trail maintenance.

The Front Runners New York Cross Country 5K will take place in Bronx County on Saturday 26 September 2026. You can run 5 kilometers.

Experience a scenic trail run through wooded hillsides and fields near the Wallkill River. Choose between a 5k or 10k race on single track trails and participate in the local athletic sneaker recycling program.

Experience a massive endurance test at Mohawk Mountain Ski Area. This ultra trail event features a 152 mile course with over 72,000 feet of elevation gain to be completed within 84 hours.

Test your limits on a flat one mile loop at the Sussex County Fairgrounds. Choose from 6 to 72 hour timed races or certified marathon and 50K distances with full kitchen and shower access.

This 24-hour trail challenge in Cornwall, CT, covers over 28 miles and 13,685 feet of elevation gain. Participants can run, hike, or walk the double marathon distance or tackle it as a relay.

A 30 hour looped trail ultra at Roosevelt Forest in Stratford, CT, run on a 2.23 mile lap with roots, rocks and a notable hill. Multiple distances are offered and awards are based on most miles completed during the time limit.

Run through 300 acres of scenic vineyards on a flat trail course in Peconic. Enjoy live music, food trucks, and a post-race glass of wine at this chip-timed autumn event.

Experience the wooded trails of Irvington during this four mile race. Navigate a course featuring elevation changes and natural turns through the local forest landscape.

A multi-day trail event near Rocky Point, NY, run on a 10.48-mile loop with distance options from 10 miles to 150 miles. Two staffed aid stations provide food and volunteer support; pacers and crews are allowed with prior notice.

A trail 5K and 1 mile accessible run in Wilton, CT on 10/10/2026 with participant T-shirts, on-site food and entertainment, spectator options, and sponsor levels; proceeds support the Prospectors mission for employment opportunities.

Experience a premier 13.1 mile trail race through the woods of New Rochelle. This half marathon takes runners across local trails for a focused off road experience in New York.

Run or walk through the scenic trails of Blydenburgh Park this autumn. Participants enjoy a 5K trail course complete with seasonal treats and commemorative event swag.