Trail Running calendar near Red Hook 2026-2027

Trail races at Thacher State Park on August 23, 2026, with 10K, half marathon, marathon, and 50K options that share the same opening 10K loop. The event is cupless with multiple aid stations and race day packet pick up.

A 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco on August 23, 2026, with start and finish at the Fox Lane High School campus and a non-perishable food collection for the Mt. Kisco Food Pantry.

Experience Stratford’s dirty day on the beach at this 5k obstacle race featuring 18+ challenges through sand and water to support the Sterling Community Center.

A trail event in Rosendale, NY on the Shawangunk Ridge Trail offering 70 mile, 30 mile, and half marathon divisions. The course crosses varied terrain and is minimally supported so participants must carry food and water purification.

Trail race at Macedonia Brook State Park on 13 September 2026 featuring single-track forest trails, climbs, viewpoints and three distances: 50K, 25K and 12K.

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.

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.

A point to point trail marathon in the Catskill Mountains with almost 7,000 feet of elevation gain, multiple aid stations, finishline food and proceeds that support land conservation. Registration opens May 1, 2026.

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 an ultimate endurance test at Mohawk Mountain by taking on 61 miles and 29,155 feet of elevation gain. Participants have 72 hours to run hike or walk their way to an Everest sized vertical achievement.

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.

A 4 mile trail race through the Irvington Woods on October 4, 2026, with varied terrain and stairs. Start and finish are at the back soccer field of Irvington High/Middle School; registration runs March 15 to September 4 with a $40 fee.

The Trailwagger offers scenic runs through Gilbert Lake State Park, with distances from 3 to 8 miles and a team option. The event supports a local animal charity and even includes a dog walk. It's a fall event with options for different pac..