New York
New York Trail Running Calendar 2026-2027
Explore the best trail runs in New York for 2026-2027! Our updated list features 160 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
Scenic fall 5K and 8K at Pindar Vineyards in Peconic NY with chip timing, water stations, postrace wine for 21 plus, live music and food trucks.
A 4 miles trail race through Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus.
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.
Trail half-marathon in Cold Spring, NY on October 4, 2026 covering 13.7 miles with 4,000 ft of climbing through the Hudson Highlands; proceeds help NYNJTC.
A trail 5K at CCC Camp in Winona Forest supporting Friends Forever Animal Rescue, featuring an off pavement course, awards and a post race BBQ.
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.
Half marathon and 6K in Rosendale NY on the Wallkill Valley Rail Trail with the historic Rosendale Trestle; proceeds support 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-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.