Wading River
Trail Running Calendar near Wading River 2026-2027
Explore the top trail runs near Wading River for 2026-2027! We've gathered 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A 2.5 mile trail run and walk at Wildwood State Park on August 8, 2026, held rain or shine. Registration fees and a donation option are listed, and personalized bibs are available for those who register three weeks in advance.
Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.
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-hour trail ultra at Roosevelt Forest in Stratford CT with 2.5-mile loops, buckles at 100 miles, and a 50 participant field limit.
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 repeated for distances up to 150 miles, with two stocked aid stations and crew support.
A scenic 5K trail run and walk at Blydenburgh County Park on October 11, 2026 with in-person and virtual options. Participants receive a race tee, on course hydration and age group recognition while proceeds benefit a local running foundation.
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
Shore2Shore in East Islip, NY on April 17, 2027 follows the Greenbelt from north shore to south shore and offers 50K and 25K distances.
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.