Trail Running calendar near Cold Spring 2026-2027

Tackle a scenic 5K or 8K through Pindar Vineyards on flat packed trails while supporting the NY Cancer Foundation. Finish with live music, food trucks and a complimentary glass of Pindar wine for a festive fall celebration.

A multi distance trail event in Rocky Point, NY from October 9 to October 12, 2026, run on a 10.48 mile loop with two aid stations. Distances range from 10 mile to 150 mile and runners must complete the distance they start.

Trail races at Mohawk Mountain Ski Area in Cornwall CT offer 5K, 10K, half marathon and marathon courses across ski trails and Mohawk State Forest, with notable elevation gain, cupless aid policy, finisher medals and overall awards.

A single-loop half marathon through five parks in lower Westchester County, New York, starting at the Thomas Paine Cottage and finishing at New Rochelle High School. Mostly shaded dirt trails with varied wildlife and published race results.

A two day running event in Bay Shore, NY featuring marathon, half marathon, 10K, 5K, kids runs and a virtual challenge. Proceeds benefit local veterans and the event has raised over $1,000,000 to date.

The Tom Centinaro Memorial "Dam" Race will take place in Waterbury on Saturday 17 October 2026. You can run 4 miles.

A fall trail half marathon and 10K through Harriman State Park on October 18, 2026, featuring technical singletrack, steep climbs, and marked aid stations. The event supports the New York and New Jersey Trail Conference and is capped at 175..

Run Clinton Road with volunteer zombies and themed aid stations for a spooky, fun challenge this October. Choose a Zombie Crawl, 5k or 10k and celebrate at the finish line festival with music, a costume contest and a Survivor Medal for all..

A 5 mile trail race at Muscoot Farm in Katonah with two kids races by age group, Farm Bucks for the farmer's market, optional shirts, and no dogs permitted except trained service dogs.

A weekend trail event at Red Wing Recreation Area in Lagrangeville, NY offering 10K, 50K and 100K loop races with continuous aid, finisher medals, and UTMB Index designation for the 50K and 100K.

Timed trail event at Gurski Farm in Brookfield CT featuring continuous 4 mile loops for 8 hour and 4 hour runners plus new 5K and 5K Canicross options. Post race food and beverages are provided.

Trail marathon and half marathon in Rockefeller State Preserve with start and finish at Rockwood Hall. Courses use wide, groomed carriage roads and offer run and walk options with charity bib entries.

A trail 10k at Ward Pound Ridge Reservation paired with a November virtual 100k challenge that rewards finishers with a custom engraved woodallion; the race uses rocky ridgeline trails and includes an on-course water stop near the fire towe..

A technical trail event at Tarrywile Park in Danbury offering 10K, half marathon and marathon distances with significant elevation gain; finisher medals, podium awards, and post-race food are provided.

A trail half marathon in Roosevelt Forest on November 21, 2026, run as eight 1.64 mile loops over singletrack and doubletrack with roots, rocks, and rolling hills. Costumes are encouraged and a book drive supports Books4Everyone.

Take on a rugged 5 mile lollipop loop in Lewis Morris Park with rocks, roots and about 600 feet of climb for a true trail challenge. Limited to 120 runners, the cupless, eco friendly event features reusable cups and hemp race bibs.

Join the Soul n Body Thanksgiving Trail Run in Wolcott CT for a spirited 3.5 mile loop around Mill Pond Way, complete with finisher medals, swag and post race yoga. Proceeds benefit endometriosis research and furry friends are welcome.

Squatchy Leftovers on November 28, 2026 at South Mountain Reservation in West Orange, NJ offers looped trail races from 5K to 50K on a mixed carriage road and singletrack course, supports Bigger Than The Trail, and includes family friendly..

Hit the trails at Rob's Trail Run Edition in Woodbury on Sunday, November 29, 2026. Choose a 5K for adults or youth and enjoy scenic singletrack through Stillwell Woods Preserve.

A timed out and back event on the Tower Trail at Sleeping Giant State Park where runners repeat roughly 3.3 mile laps to the Observation Tower in four hour or eight hour formats. Aid is at the start and finish and the race follows a cupless..