Trail Running calendar near Wallingford 2026-2027

A technical trail half marathon and steep 10K in Harriman State Park with significant elevation gain. Registration supports the New York and New Jersey Trail Conference and hardship and discount options are available.

Experience a unique 50k trail race through interconnected woodland preserves in southern Connecticut. This single loop course features rocky forest roads and single track trails designed to test your endurance and mental stamina.

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.

Trail event at Mt Tom State Park on October 24, 2026 offering 25k and 10k courses, a 25k two person relay, and an untimed 5k fun run or hike. Proceeds support Kestrel Land Trust conservation work.

Experience a unique trail race through the forests and meadows of Muscoot Farm. Enjoy distances for all ages followed by a visit to the local farmers market with your farm buck vouchers.

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.

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 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 trail event at YMCA Camp Sloper on November 21, 2026, offering a 400 minute timed loop option and a two mile two lap race, with 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..

A 5K run and walk through Inwood Hill Park in northern Manhattan with a shared start and finish, live results and free finish line photos. Proceeds benefit the Inwood Food Pantry and awards are given to the top two men and women.

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.

Repeat a 3.3 mile out and back up the Tower Trail to the Observation Tower at Sleeping Giant. Runners choose a four hour or eight hour format, carry their own hydration, and complete as many laps as they can within the time limit.

A looped ultramarathon in Prospect Park, Brooklyn offering 50 mile and 50 kilometer options. The course uses 3.33 mile loops and includes on course hydration and a potluck style aid station.