Trail Running calendar near Roxbury 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 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.

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.

The Thompson Turkey Trot will take place in Thompson on Sunday 8 November 2026. You can run 5 kilometers.

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.

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, part of the NYRR Cross Country series, with live app tracking, on-site awards, a member standby list, and youth programming for ages 2 to 18.

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.

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 trail party on November 28, 2026 at South Mountain Reservation in West Orange, NJ, featuring 5K, 10K, 25K, 50K and a Kids 1M on a 5K loop. The course mixes carriage roads and technical singletrack and supports Bigger Than The Trail.

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.

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.

The SRC Presents: a Backyard Ultra will take place in Smithtown from Saturday 12 December 2026 to Sunday 13 December 2026. You can run 4 miles.

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.