Trail Running calendar near Windham 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 50K trail ultramarathon in the Wilcox Lake Wild Forest near Stony Creek, NY, with a lollipop route, about 3,028 feet of climb, two stocked aid stations, and a required experience review for entry.

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.

Trail races in Charles E Baker State Forest near Brookfield, NY offering 5K, 15K and a 50K with 4,600+ feet of vertical gain and a 9 hour cutoff. Onsite grilled food supports the Brookfield Central School Senior Class.

Timed trail races at Lakeside Park in Pawling, NY on an approximately 1.68 mile loop with 3, 6, 12 and 24 hour options, cupless format, aid station supplies, finisher medals and specific support and pacer rules.

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.

This fifth annual 5K in Dolgeville follows the scenic Greenway Trail through the forest. Registered participants get a free t-shirt, and post-race refreshments are provided. All proceeds go to providing free sports equipment for local youth..

A trail running event in Gardiner, NY offering a 5 km run, an optional 10 km two-lap route and a 200 yard kids run, with pre registration T shirt incentives and a 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.

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 fall endurance event in Cohoes, NY offering 6 hour solo and relay, 3 hour and 1 hour timed formats, with buckles for solo runners over 26.2 miles, swag and finisher awards, and fundraising for Flutters of Hope Inc.

Trail races and a half marathon take place around Barbour Woods and Haystack Mountain in Norfolk, CT on October 4, 2026. Routes include single track and carriage roads and the half marathon features over 2000 feet of elevation gain.

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..

A running race at Mohawk Mountain Ski Resort in Cornwall CT on October 11 2026, organized by Steep Endurance in cooperation with the ski area, with entry fees ranging from 30 to 95 USD.

A fall trail running event at Harriman State Park on October 18, 2026 offering a technical **13.1M** and a hilly **10K**, with marked singletrack, two aid stations for the half, a five hour finish cutoff, and limited field size.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

Experience the wilderness trails of Deerfield Town Park with a variety of trail races for all ages. Enjoy a professionally timed 5K or a community run while supporting the local food pantry in your favorite running costume.

A fall trail event at Muscoot Farm in Katonah on October 25, 2026 featuring a five mile trail race and two kids races. Participants receive Farm Bucks for the farmer's market and shirts are available by preorder.