Trail Running calendar near Windham 2026-2027

Experience a unique timed trail event at Gurski Farm featuring a four mile loop of rolling farm trails and single track. Choose between eight hour, four hour, or 5K options in a community focused environment.

A trail event at Ward Pound Ridge Reservation combining a 10 kilometer trail race with a November virtual 100k challenge, volunteer support, postrace results, and a finisher woodallion for reported 100k totals.

Trail races at Tarrywile Park in Danbury, CT offering 10K, half marathon and marathon options on technical single track; the half uses a loop with close to 3K of elevation and a cupless race policy.

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.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

A mountain trail event at Harriman State Park offering a half marathon, a 10K, and a 10K ruck on rugged, technical courses with significant elevation gain and limited crew access at aid stations.

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A weekend obstacle course at Mountain Creek Resort in Vernon NJ on April 24–25, 2027, offering Sprint 5K, Super 10K, Beast 21K, Ultra 50K and kids races, plus a Trifecta Weekend option and team entries.

Two mountain trail races in the Shawangunk Ridge on April 24, 2027. The technical 25K and 10 mile routes feature cliffs, steep climbs, two aid stations, strong course markings, and a 150 participant cap.

A mountain trail festival near Ellenville NY offering a technical 25K (about 17 miles) and a 10 mile course, both limited to 150 entrants with a six hour cutoff. The routes feature steep climbs, rocky singletrack, and two stocked aid statio..

XTERRA New Jersey on April 24 and 25, 2027 brings trail runs, triathlon, duathlon, paddle tri and mountain bike races to Stokes State Forest, with World Tour and Trail Run World Series events and World Championship qualification slots.

A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.

A community 5K in Ellenville starting and finishing at Aroma Thyme Bistro, with a course along the base of the Shawangunk Mountains and a stretch on the newly resurfaced Rail Trail. Proceeds benefit local food pantries and youth scholarship..

An obstacle race weekend at Bethel Woods in June 2027 featuring Sprint, Super and Kids races across rolling hills and classic obstacles; teams can secure shared start times and eligible U.S. service members may receive a discount.

A mountain trail event at Plattekill in Roxbury NY on June 6, 2027, featuring a 6.5 mile course with 3500 ft ascent and a steep 5k. Awards and finisher swag are planned for top finishers.