Trail Running calendar near Pawling 2026-2027

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 featuring a marked 10k race and a monthlong Raven 100k November Challenge. The course includes rocky climbs, ridgeline trails and a water stop near the Fire Tower climb.

A community 5K and 1 mile walk on November 8, 2026 at Central Park of Morris County supporting Family Promise of Morris County, with in-person and virtual 5K options and age-group awards.

A charity trail event at Hillside Park on November 8, 2026, offering 10 km and 5 km races to benefit a free digital mammography program, with race timing, age-group medals and participant T-shirts.

A trail running event on Staten Island with 50 mile, 50K and half marathon loop courses through the Greenbelt, featuring staffed aid stations and support for the Greenbelt Conservancy.

Experience the diverse terrain of South Mountain Reservation with a looped trail race offering 5K, 10K, and half marathon distances. Enjoy a mix of single track and fire roads with support provided at regular aid stations.

A 5K run and walk through Bethpage State Park on November 14, 2026 with a free kiddie dash, post-race refreshments and finisher photos. Virtual entries can submit times and photos from November 14 to 22.

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 scored 5K cross country race at Van Cortlandt Park on November 15, 2026, as part of the NYRR series. The event includes youth Rising NYRR activities, live runner tracking via the NYRR app, and on-site awards for top finishers.

The Last Chance XC Championships will take place in Clark on Sunday 15 November 2026. You can run between 5 and 8 kilometers.

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 in Southington CT offering a timed 400 minute loop challenge and a two lap four mile option, chip timing, a main aid station, and proceeds benefitting local organizations.

A *5 miles* lollipop loop trail race in Lewis Morris Park, Morristown NJ, run mostly on the Yellow Trail with roughly 600 feet of elevation gain. The event limits entries to 120 runners, uses cupless stations and hemp bibs, and offers free..

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 5K run and walk through Inwood Hill Park in New York with live results, free finish line photos, and awards for the top two men and women; proceeds support the Inwood Food Pantry.

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.

A November trail party at South Mountain Reservation offering looped distances from a Kids 1M to a 50K, varied carriage roads and singletrack, on-course aid at the start/finish, adaptive support, and a charity partnership with Bigger Than T..

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.

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.

Trail races at South Mountain Reservation feature 5K, 10K and 13.1 miles on looped courses over fire roads, single track, hills and pavement, with aid about every three miles and race day registration available.