Trail Running calendar near Baiting Hollow 2026-2027

Run or walk through 50 acres of beautiful vineyards in Peconic for a chip timed 5K event. Participants receive a finisher medal that doubles as a wine stopper and a celebratory pour of wine at the finish line.

A classic 16-mile trail run on Connecticut's Nipmuck Trail, known for its technical terrain and old-school vibe. Organized by the Shenipsit Striders, the event supports local trail stewardship. Registration is capped and no race day signups..

Experience a variety of technical trails and rock scrambles in Connecticut at the Sleeping Giant Trail Runs. Choose between 25 km and 50 km distances featuring significant elevation gain and historical park landmarks.

Mudders and Grunters is a trail race in Yorktown Heights on March 29, 2026, featuring an approximately 5 mile single loop through mud, water crossings and some hills. It is part of the 2026 Trail Mix Series.

Experience a technical trail race through the rugged and hilly terrain of Van Cortlandt Park in the Bronx. Enjoy 10k or kids distances with cake prizes for top finishers and support local trail maintenance efforts.

Run the perimeter of Heckscher State Park on smooth trails. Choose a 7-mile or 14-mile loop for a cupless, manually timed race. All finishers get a wooden medallion and a bucket hat.

Experience a scenic trail run through Bethpage State Park with the 4 Leaf Clover 5K. Enjoy a mostly flat course, post race refreshments, and a festive atmosphere supporting the Never Stop Running Foundation.

Experience a technical mountain trail race at Harriman State Park featuring steep climbs and rock scrambling. Choose between 10K and Half Marathon distances with stunning views of the Hudson Valley and NYC skyline.

Experience the 7th Annual Bunny Trail 5K at Bethpage State Park. Run or walk through scenic soft trails and grassy polo fields with options for an in person race, a virtual challenge, and a free kids run.

Experience an authentic off road adventure in Guilford with a 10k trail loop featuring technical single track paths and rock scrambles through Westwoods to support local land conservation.

Run a unique quarter marathon distance on the paved trails of West Hartford Reservoir. This chip timed 6.55 mile race features a two loop course with post race treats and age group awards.

Join this dog friendly 5K trail run at Blydenburgh County Park to support animal rescue. Enjoy a scenic multi surface course with refreshments and professional timing included for all participants.

Experience a community trail event in Cross River featuring a competitive 5k race, a scenic 4k walk, and a 200m kids dash. Explore the wooded hills of the John Jay Community Trail ending at the campus contest field.

Experience a unique all terrain run through Heckscher Farm and wooded trails in Stamford. Runners pass farm animals and historic landmarks on a scenic course while children enjoy a dedicated fun run and educational activities.

Experience a beautiful trail run through the Irvington Woods with 5K and 1K distances. This rain or shine community event features finishers medals for all participants and supports the Irvington Bulldog Booster Club.

The Shore2Shore is a scenic point-to-point trail run on Long Island's Greenbelt Trail, from the north to south shore. Choose between the 50K or 25K distance on this well-marked course. Registration includes a trail work volunteer requiremen..

The Traprock 50 features a rugged 50K and a 17K trail race on the rocky, rolling loops of Penwood State Park. It's a cupless event with chip timing, organized by volunteers to benefit local conservation groups. Runners should be prepared fo..

The final Conquer the Trail Race is a 7.5 km run on the flat Croton Aqueduct Trail. This special edition supports Mercy University's Mav Market and celebrates the school's 75th anniversary. The event offers awards, raffles, and free parking..

The Brookhaven Trail 15K and 4 Mile runs explore the varied paths of Brookhaven State Park. This cupless event is capped at 250 runners and includes awards, refreshments, and supports veterans and local food banks.

Experience a women and non binary trail race at Lake Mohegan in Fairfield. Choose between 5K and 10K distances or a 4 hour timed challenge on a scenic loop.