Trail Running calendar near Hauppauge 2026-2027

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

Trail race in Macedonia Brook State Park, Kent CT offering 12K, 25K and 50K loop courses with significant elevation, aid stations, and a cupless policy.

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

Timed trail races in Pawling NY offering 24, 12, 6 and 3 hour options on an approximately 1.68 mile loop with on course aid and athlete camping.

A multi-day trail running festival in Ringwood State Park offering events from a 1 mile kids race to a 100 mile ultramarathon and community support programs.

A USATF-sanctioned trail event in Upper Nyack with a 50 mile option featuring four 11.5 mile loops, about 9,700 feet gain, and three aid stations.

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 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

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.

A 5th annual 3.1-mile run and 1.1-mile walk at The Church of St. Andrew in Staten Island, and the first leg of the Staten Island FALL TRIFECTA.

Technical trail races in Burlington CT on the Tunxis Trail offering 8K and 5K courses that pass the CT State Trout Hatchery and Nassahegan State Forest.

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.

A six-hour run and relay at Belmont Lake State Park honoring Fred von der Heydt with individual and team competition on a 1.50 mile loop and commemorative apparel.

A scenic 3.1-mile road and trail run through the New York Botanical Garden, featuring forest and garden views, post-run festivities, and an included All-Garden Pass.

A scored 5K cross country race at Van Cortlandt Park in the Bronx on September 27, 2026, part of the NYRR Cross Country Series with youth and accessibility programs.

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.

A 24 hour Backyard Ultra trail event at Mohawk Mountain Ski Area in Cornwall, CT, featuring about 14,400' of elevation and options to run, hike or walk.

A 30-hour trail ultra at Roosevelt Forest in Stratford CT with 2.5-mile loops, buckles at 100 miles, and a 50 participant field limit.

A six week 5K cross country series in Monmouth County parks with team and age group scoring, series prizes and both pre registration and event day registration.

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.