New York
New York Trail Running Calendar 2026-2027
Explore the best trail runs in New York for 2026-2027! Our updated list features 179 exciting trail runs across the region. Find your next trail run in New York below and join the trail community at these great events!
October 2026
A 3.1 mile trail run through the Great Swamp Conservancy habitat center in Canastota, NY on October 4, 2026; registration opens July 27 and costs $25.
Experience 13.7 miles of Hudson Highlands trails with 4000 feet of elevation gain during the peak foliage season in Cold Spring New York
A fall trail 5K in Winona Forest that supports Friends Forever Animal Rescue, featuring an all-off-pavement course, on-site timing, awards, a post-race BBQ, and the option to add a donation during registration.
Scored cross country 5K at Van Cortlandt Park in the Bronx, part of an NYRR series that includes youth races, accessibility provisions, and official results via the NYRR app.
Trail runs of 3.1 miles and 6.2 miles take place at Genesee County Park and Forest on October 4, 2026. Proceeds support ACORNS and a portion will go to breast cancer research.
A half marathon and 6K on the Wallkill Valley Rail Trail in Rosendale, NY, featuring the historic Rosendale Trestle and proceeds benefiting the Wallkill Valley Land Trust.
Trail 5K at Buried Barrel in Castile NY on October 4, 2026 with in-person and virtual options, a point-to-point finish in Pankow Farms orchard, swag, awards, and local charity support.
A stair race up the Empire State Building's 86 floors and 1,576 stairs in New York with several entry categories and set registration windows and fees.
Four-day trail event in Rocky Point, NY featuring a 10.48-mile Pine Barrens loop with eight distance options from 10 miles to 150 miles.
Trailwagger at Gilbert Lake State Park offers 3 mile, 5 mile, an 8 mile combined option, a team division, and a dog walk supporting Super Heroes Humane Society.
Trail runs in Danby State Forest offering 10K and 23K courses on singletrack with Thatcher Pinnacles views, marked turns, aid stations, and post-run refreshments.
Off-road 4 and 8 mile runs at Holiday Valley Resort on October 10, 2026, starting from the hilltop via chairlift, with limited entries and after-race refreshments.
A community 5K with kids and youth runs at Pitney Meadows Community Farm featuring mixed grass and stone dust trails and proceeds supporting the farm.
Scenic 5K at Rockefeller State Park Preserve featuring hilly carriage roads, age group and team awards, t shirts and refreshments, with proceeds supporting carriage road maintenance.
Trail half marathon in New Rochelle running a single loop through five Westchester parks on mostly dirt shaded trails with frequent wildlife on October 11, 2026.
Pickle themed Halloween obstacle event at Obstacle Wonderland in Wallkill NY with adult 5K, kids 1K, a pumpkin carry fundraiser, themed medals, and family friendly activities.
Trail 5K at Blydenburgh County Park on October 11, 2026 offering in person and virtual options, participant tees, refreshments, and age group recognition.
A 5K race at Veeder Tree Farm in Earlton, NY on October 11, 2026, with proceeds benefiting the Leukemia and Lymphoma Society.
A fall trail event at HoliMont featuring a summit chairlift start, a 5K and kids loop, a costume contest, awards, and food and drink at the finish.
Run a 5K through the private 157 acre Rochester Rotary Sunshine Camp on a mix of dirt trails and paved paths. Enjoy the post race Beer Fest and support accessible camping for children with disabilities.