New York
New York Trail Running Calendar 2026-2027
Explore the best trail runs in New York for 2026-2027! Our updated list features 147 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 Halloween-themed team scavenger hunt run at DeWolfe Brewing in Victor on October 22, 2026, where teams complete checkpoints, post photos to earn points, and can earn bonus points.
Trail races in Allegany State Park near Salamanca NY offering 50 mile, 50 km and 25 km distances, aid stations, USATF sanction and UTMB Index status.
Outrun the Stigma 5K Run/Walk in Massapequa Park on October 24, 2026 features a 5K and kids fun run with medals, awards, photos and an after party.
A 5K trail race at Bella Rose Winery in Lewiston on Oct 24, 2026, running through vineyards with a post-race celebration; net proceeds benefit Feedmore WNY.
Trail event at Muscoot Farm on Oct 25, 2026 with a 5 mile race, two kids races, Farm Bucks and medals for young finishers.
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.
Autumn races in Garrison NY featuring a half marathon, 5K and a 3/4 mile kids run with a course through Hudson Highlands and past Osborn Castle.
Celebrate Halloween with a 5K trail run or a kids fun run at Green Lakes State Park featuring costumes candy and a festive trunk or treat session.
A community fundraiser at The Y at Watson Woods on 10/25/2026 featuring a two hour lap-based trail race, raffle tickets, a chili cookoff and a costume contest.
A community 5K run/walk in Forest Park, Queens on October 25, 2026, with a free 1K kids run, participant T-shirts, and medals for early registrants and top finishers.
A single-loop 5K trail run on Schulze Vineyard & Winery property with RFID timing, on-site post-race snacks and music, free parking, and awards for overall and age-group finishers.
An out and back run from Dryden Creamery along the Dryden Rail Trail with timing, finisher treats, costume awards and family registration options.
Obstacle course weekend at Sunflower Valley Farm in New Hampton NY with Sprint, Super and Kids races plus an obstacle workshop and Hurricane Heat formats.
Trail races at Red Wing Recreation Area Oct 31 to Nov 1 2026 offering 100k, 50k and 10k looped courses with aid stations and finisher medals.
A trail half marathon in Moreau Lake State Park covering roughly 14 miles of technical singletrack with about 2700 feet of climb and one aid station at Bonita Lake.
A Halloween trail event in Rosendale with a timed 5k, a 2k walk and a free 1k kids run at Fifth Lake Hudson Valley.
A 5K event on October 31 at Word of Life Ranch in Pottersville with trail and road sections, guaranteed shirts for early registrants, awards for top finishers and costumes, and finish-line refreshments.
A Halloween-themed trail run at The Winery at Marjim Manor featuring a scenic 3.3 mile loop through orchards, costume prizes, timed results, and a post-race celebration.
November 2026
A 5 mile trail race through varied terrain in Saratoga Spa State Park on November 1, 2026, with limited entries, age group awards, and post race drawings. Registration options include online pre-registration and cash or check on race day.
Three-person trail relay at Brantling Ski Mountain in Sodus NY on 11/01/2026, each teammate runs a 2 mile loop; entry $90.00 includes an event shirt, finisher medal and post race beer.