Trail Running calendar near North Fork 2026-2027

A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.

Trail races at Red Wing Recreation Area in Lagrangeville, NY, featuring 100k, 50k and 10k looped courses with notable elevation. The 50k and 100k are UTMB Index races and all finishers receive custom medals.

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.

Experience a single loop marathon or half marathon on historic carriage roads in the Rockefeller State Preserve. Enjoy views of the Hudson River and stone bridges on a course with no pavement or cars.

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.

A Thanksgiving themed chip timed 5k at Stonington Vineyards on November 8, 2026. The event features vineyard scenery and includes a t shirt, a portable wine glass, a finisher medal that doubles as a wine stopper and a wine pour.

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 November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.

Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.

Trail races at YMCA Camp Sloper on November 21, 2026 include a 400 minute timed event and a four mile two lap race, with a flagged two mile loop, aid station, chip timing, and capped fields.

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.

A community 5K run and walk at Inwood Hill Park near 600 West 218th Street in New York City, with live results, free finish line photos, and proceeds supporting the Inwood Food Pantry.

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

A looped road ultra in Prospect Park, Brooklyn on Dec 6, 2026 offering 50-mile and 50k options over 3.33-mile loops, with a 15 hour cut-off, Skratch Labs hydration, pot-luck aid, and finisher buckles.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

The Ospreys Dominion Wine Run 5K will take place in Northville on Saturday 20 March 2027. You can run 5 kilometers.

A trail 5K and free kiddie run at Bethpage State Park with soft trails, event shirts, post race refreshments and a virtual option; proceeds support the Never Stop Running Foundation.

On March 28, 2027 this roughly 16 mile out and back follows the Nipmuck Trail through Yale Myers Forest and Bigelow Hollow State Park. Registration opens Jan 1, 2027, parking is limited and a waitlist is used.

A community 5K run and walk at Bethpage State Park on scenic soft trails, with a free kiddie run and a virtual option. Proceeds support the Never Stop Running Foundation.

Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT features a 25K loop with 3K+ of vertical and a 50K two-loop option. The course mixes technical singletrack and carriage roads, includes aid stations, and follows a cupless..