Trail Running calendar near Wading River 2026-2027

A fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.

A fall trail event at Muscoot Farm in Katonah on October 25, 2026 featuring a five mile trail race and two kids races. Participants receive Farm Bucks for the farmer's market and shirts are available by preorder.

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.

Experience the Fall Back Into The Trails Series at Red Wing Recreation Area in Lagrangeville. Choose from 100k, 50k, or 10k distances featuring a loop course with elevation gain. This UTMB Index event offers medals and awards.

A timed trail event at Gurski Farm on a 4 mile loop of single track and farm trails. Options include an 8 hour race, a 4 hour race and a 5K plus 5K canicross; the event is cupless with aid at start finish.

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 running event at Ward Pound Ridge Reservation with a ten kilometer race and a November 100 kilometer virtual challenge. The course features rocky climbs, ridgeline views, and a custom finisher woodallion for challenge completers.

USATF Long Island hosts Open, Masters and Para Athletic cross country championships over an 8K course on November 8, 2026. Online registration is closed.

A Thanksgiving themed timed 5k run and walk at Stonington Vineyards on November 8, 2026 featuring vineyard scenery, chip timing by J3 Timing, event shirts, a collapsible wine glass, a wine glass shaped finisher medal and a pour of wine.

A multi-loop trail event on Staten Island offering a half marathon, 50K, and 50-mile courses that pass through Blood Root Valley, High Rock Park, and La Tourette Park, with proceeds supporting 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.

Experience a seasonal 5K trail run or walk through the scenic paths of Bethpage State Park. This family event features local refreshments and a welcoming atmosphere for participants of all abilities.

Trail races at Tarrywile Park in Danbury, CT offering 10K, half and marathon on technical single track with significant elevation. Finisher medals, awards and a cash bonus for fast half marathoners.

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.

A trail half marathon in Roosevelt Forest featuring eight laps of a 1.64 mile wooded loop with roots, rocks, and rolling terrain. The event includes a book drive, costume prizes, event swag, and podium awards for top finishers.

A timed multi-loop trail event at YMCA Camp Sloper in Southington with a 400 minute unlimited-loop option and a separate 4 mile race, chip timing, a central aid station, and proceeds supporting local organizations.

A community Thanksgiving event featuring a 3.5 mile run and walk around Scoville Reservoir in Wolcott CT, with multiple start waves, post race yoga for participants, finisher medals, volunteers supporting refreshments, and proceeds to EndoF..

Celebrate the holiday at the Inwood Hill Turkey Trot 5K Run and Walk. This event offers a scenic course through Inwood Hill for participants of all abilities to enjoy a morning of fitness and community.

A trail party at South Mountain Reservation offering looped 5K terrain and distances from Kids 1M to 50K. The course mixes carriage roads and technical singletrack and features an aid station at the start finish and a charity partner.

Enjoy a post holiday run or walk through the scenic trails of Bethpage State Park. Participants earn themed swag and enjoy refreshments from local partners at this festive 5K event.