New York
New York Trail Running Calendar 2026-2027
Explore the best trail runs in New York for 2026-2027! Our updated list features 151 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 stair-climb race at the Empire State Building ascending 86 flights (1,576 steps) with multiple entry categories and specified registration windows.
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 on October 10, 2026 at Gilbert Lake State Park offers 3, 5 and 8 mile courses plus a dog walk, with proceeds supporting the 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.
A scenic October 5K on the carriage roads of Rockefeller State Park Preserve with hilly terrain, awards, and 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 in Wallkill, NY with a 5K adult course and 1K kids course, themed medals, costumes encouraged, and a zip line finish.
A scenic trail 5K at Blydenburgh County Park on October 11, 2026 with in-person and virtual options, race tee, refreshments, and age-group recognition.
A 5K event in Earlton on October 11, 2026 offering both road and trail 5K options plus student and combo entries, with proceeds to the Leukemia and Lymphoma Society.
A fall trail event at HoliMont in Ellicottville with a 5K downhill course, a kids mile on the mountaintop, lift access and a costume contest.
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.
Multi day running weekend in Bay Shore, NY with marathon, half marathon, 10K, 5K, kids 1K, relay and a virtual 26.2 miles challenge.
A Halloween-themed 5K on the Lehigh Valley Trail in Mendon, NY with in-person and virtual options, a costume contest, prizes, and a post race brew.
A 12-hour fixed-time night race on a paved 2.06-mile out-and-back on the Lake Ontario State Parkway Trail with required headlamps and an all-night aid station.
HHNC Meadows & Trails 5K is an off road 5K at Hudson Highlands Nature Center in Cornwall NY on 10/17/2026, featuring meadows, ponds, wooded trails and views of Black Rock Mountain. Entry is $35 and children under 18 run free.
Timed 6, 12, and 24 hour ultraruns on a flat 0.30 mile campground loop at Champs Campground & RV Park in Whitehall, NY, limited to 20 runners per division.
Two 5K trail races at Ganondagan State Historic Site in Victor NY with a canicross class and a dog friendly 5K, timed results, medals, and age group awards.
Night trail event at Dryer Road Park with a glow marked 5 mile course and a 1.5 mile fun run for kids and families on October 17, 2026.