Trail Running calendar near Wading River 2025-2026

CT Donut Run is a 31.5-mile charity group run in Connecticut, presented as a long, donut-filled endurance experience rather than a traditional race. The route centers in West Hartford and visits several donut stops, including locations in Newington, Berlin, Wallingford, and North Haven, finishing in..

The Run the Vineyards - Pindar Fall 5K and 8K is a scenic autumn race held at Pindar Vineyards in Peconic, NY, featuring courses through 300 acres of vineyard property. Participants can choose between a 5K and an 8K race, both on mostly flat, hard-packed dirt trails and short-cut grass, making the e..

The Fat Sass Switchback Challenge is a trail running event held in Millburn, New Jersey, at the South Mountain Reservation's Locust Grove Picnic Area. Scheduled for October 5, 2025, it features a challenging 1-mile loop course with 300 feet of elevation gain, including steep climbs and technical, ro..

Set in Montebello, New York, the KMT Fall Foliage Frenzy is a trail-running event featuring 3-hour and 6-hour timed races. Runners tackle a challenging 2.33-mile loop with about 660 feet of vertical gain, weaving through Kakiat Park against the backdrop of Harriman State Park and the Hudson Valley’s..

NipMuck Trail Marathon, in Ashford, CT, features two options: the original NipMuck Trail Marathon (26.4 miles) and a two-person NipMuck Relay. The race uses a 13-mile middle segment of the Nipmuck Trail, running south to Route 44, back to the start, then north to Boston Hollow before finishing at Pe..

The Norfolk Land Trust Trail Race Series, including the Haystack Mountain Challenge, is held annually in Norfolk, Connecticut. The 12th edition features three trail race distances: a challenging 5K through Barbour Woods with scenic climbs and wetlands; a 10K that adds a tough loop summiting Haystack..

Tesla Hertz Run is an ultrarunning event in Rocky Point, New York, offering multiple distances on a single Long Island course: 150‑mile, 100‑mile, 100K, 50‑mile, 50K, a 10‑mile, and a night-time 10‑mile option. The course features a scenic 10.48‑mile loop through pine barren terrain, with two aid st..

The Forbidden Forest 30 Hour Ultra Run will take place in Stratford on Saturday 11 October 2025. You can run between 26 and 100 miles.

Gemstone Sparkle Sprint 5k is a community trail run in Wilton, Connecticut, on Gemstone Farm (144 Huckleberry Hill Rd). The second annual event offers a scenic 5k trail course suitable for all abilities (strollers not allowed on the course) with a festive sparkly theme inviting participants to dress..

Mohawk Mountain Race, at Mohawk Mountain Ski Area in Cornwall, CT, offers 5K, 10K, half marathon, and marathon distances. The course turns a ski mountain into a challenging trail race, with steep climbs and descents and views of fall foliage. The 5K loop climbs the left side via the Wildwood and Tim..

The Never Stop Running Foundation Great Pumpkin Dash Trail 5K is a scenic trail run/walk held at Blydenburgh County Park in Smithtown, NY. Scheduled for October 12, 2025, this event features a 5K course that winds through shaded trails combining dirt roads and hard-packed surfaces with some sandy sp..

The Paine to Pain Trail Half-Marathon is a distinctive trail race held in Westchester County, New York, starting at the historic Thomas Paine Cottage in New Rochelle and finishing at New Rochelle High School. This 13.1-mile single-loop course traverses the woods and trails of five different parks, o..

The Fred Torres Memorial 5K is the 12th annual charity race at Garrett Mountain in Woodland Park, New Jersey. The live event features a 5K run on a championship cross-country course and a 2-mile walk, with a virtual 5K option for remote participants. Family-friendly events include a Tot Trot and a 1..

Tom Centinaro Memorial "Dam" Race is a 3.5-mile trail run/walk hosted by the Wolcott Lions Club in Wolcott, Connecticut. The race unfolds on the scenic, flat Mill Pond Trail at Woodtick Recreation, 201 Nichols Road. This community event benefits local charities and the Tom Centinaro Lions scholarshi..

The Castle to River Run in Garrison, NY, is a scenic running event held in the historic Hudson Valley, featuring a half marathon and a 5K race, along with a kids fun run. The half marathon course winds through Hudson Highlands State Park, passing the historic Osborn Castle and offering a mix of sing..

Big Bear SquaTCh South, a Sassquad Trail Running event in Harriman State Park, Tuxedo, New York, features a challenging pair of trail races: a 13.1-mile half marathon and a 10K, starting and finishing at Powerhouse Park. The single-loop courses are rugged and technical, with 2,200+ ft of gain on the..

Bimblers Bluff 50K is an off-road foot race held in southern Connecticut, starting at Guilford Lakes School in Guilford. The 50-kilometer course weaves through interconnected woodland preserves on rolling forest roads and rocky single-track, offering a true test of fitness and mental stamina. Unusua..

FALL Run The Farm is a 5-mile trail race held at Muscoot Farm in Katonah/Somers, New York. The course winds through the scenic farm grounds, showcasing the area’s natural beauty and tying the event to the nearby Muscoot Farmer’s Market vibe. The day also includes Fall Kids Run The Farm for younger p..

The Grills Trail Run, hosted by the Westerly Track & Athletic Club, takes place at Grills Preserve in Westerly, Rhode Island. Scheduled for October 25, 2025, it features two race distances: a 10-mile and a 10K. Both courses start and finish at Grills Preserve, showcasing scenic trails with about 80%..

RACE FOR THE GREENWAY 5K RUN / WALK takes place at Hallock State Park in Riverhead, NY. The mostly flat off-road 5K course weaves through parkland with views of beaches, vineyards, ponds, and forests, featuring loose gravel and grass underfoot. Runners and walkers of all abilities are welcome.After..