Wading River
Trail Running Calendar near Wading River 2026-2027
Explore the top trail runs near Wading River for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
An obstacle-based 5K at Short Beach, Stratford on September 12, 2026, with 18+ obstacles and fundraising for the Sterling Community Center.
October 2026
A 30 hours looped trail ultra in Roosevelt Forest CT with multiple distance options, a 2.5 mile loop, single pavilion aid station, pacer rules, and finisher buckles at 100 miles.
Run through 300 acres of scenic vineyards on a flat trail course in Peconic. Enjoy live music, food trucks, and a post-race glass of wine at this chip-timed autumn event.
Multi-day trail event in Rocky Point NY on a 10.48 mile loop used for distances from 10 to 150 miles, with two aid stations and crew support.
An off‑road 50K around Guilford, CT on rocky single track and rolling forest roads, with aid station cutoffs and recommended marathon-level experience.
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.
November 2026
December 2026
A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.
March 2027
Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and finisher me..
April 2027
Point-to-point 50K and 25K along the Suffolk County Greenbelt Trail from Sunken Meadow to Heckscher State Park, returning April 17, 2027.
May 2027
A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.
June 2027
An inaugural community 5K and 1-mile walk at Camp Edey supporting Girl Scouts programs, with race awards, family activities, and participant amenities.
August 2027
A 2.5 mile trail run at Wildwood State Park on August 7, 2027, with live results, free finish line photos, and proceeds benefiting Friends of Wildwood State Park.