Trail Running Calendar New York 2025-2026

A three day trail stage race at Mendon Ponds Park Nov 7 to 9 featuring a hilly Pond Road time trial, a mass start stage with a stair climb, and an epic long trail finale. Run a single stage or take on the full series to earn a finisher hood..

Run the scenic Pocantico Hills Marathon or Half Marathon on Nov 8 2025 in Sleepy Hollow NY, a loop through Rockefeller State Park Preserve with rolling hills and Hudson views. Proceeds support local park and trail groups.

Run the 45th Annual Veterans Cross Country 4 km at Northport VA Golf Course on Nov 8. Enjoy an English style grass course, family friendly fun runs, and support hospitalized and homeless veterans on Long Island.

Run a scenic 10K up Mt Beacon to the firetower and back on rugged Hudson Highlands trails with steep climbs and autumn views. Part of the Beacon Bonfire festival, the race ends with refreshments, a shirt and festival perks.

Take on the Raven Rocks 10k trail race at Ward Pound Ridge, starting in the meadow and climbing to Raven Rocks Overlook and the Fire Tower Summit. Enjoy rugged woods, a rewarding downhill finish, and support for Friends of Trailside Museum.

Join the Clear Path Trail 5k at Clear Path for Veterans in Chittenango for a beginner friendly trail run with sweeping campus views. Run or walk to honor veterans and support programs that help veterans and their families.

Join Taconic Road Runners for a relaxed 6K through FDR Park on November 9, 2025, now held as a club fun run and meeting. Enjoy soft trails, commemorative running gloves and hot drinks by the warming fire while you meet fellow runners.

USATF Long Island hosts an 8K cross country championship at Bethpage State Park on Nov 9, 2025 for adults 18 and over. Competitive team and individual racing with medals and live results make for a great fall race.

Run Staten Island's scenic singletrack at NYC Trail Mix on Nov 15 2025, weaving through Blood Root Valley, High Rock and La Tourette. Choose 50M, 50K or half marathon distances and support the Greenbelt Conservancy.

Run or walk a scenic 5K at Bethpage State Park for the Never Stop Running Foundation Turkey Trail Trot, with a free Kiddie Dash and virtual option. Join November 15, 2025 to support the foundation and enjoy post race treats.

Run the Brookhaven Trail Half Marathon or 5 Mile through single track, fire trails and sandy woodlands at Brookhaven State Park near Wading River NY. Half marathoners vie for cash, a wood finisher medal and post race refreshments.

Join the 4th Annual Sargent Elementary Turkey Trot in Beacon, NY for a family friendly 5K on the scenic Long Dock Park trails plus a Kids Fun Run on campus. Enjoy a food drive, live DJ, refreshments, awards and new team sign ups.

Join a scenic trail 5K or bring kids to a fun run at Hilltop Hanover Farm, a historic working farm and environmental center. This family fun fundraiser gives 5K finishers a $5 farm stand credit and supports the Friends of Hilltop.

Run a scenic trail half marathon around two glacial lakes and along the Shawangunk Ridge at Minnewaska State Park, with sweeping views into five states. Limited to 300 runners, chip timed with a finisher gift and refreshments.

Run or walk the Batavia Turkey Trot 5K on Thanksgiving Day and support Crossroads House. Family and stroller friendly with costume prizes, hot drinks and snacks after the race.

Join the Gratitude Run on November 27 at Rochester Rotary Sunshine Camp in Rush NY for a chip timed 5K, 1 mile, kids dash, or virtual race. Enjoy shirts, mile marker refreshments, and support the Sunshine Camp for children with disabilities..

Join the Cazenovia Turkey Trot on Nov 27, 2025 for a chip timed 5K or 1 mile fun run along the scenic Gorge Trail. Family friendly event benefits Caz Cares and kids 12 and under run free.

Join Somers' 7th Annual Thanksgiving Turkey Trot for a scenic but challenging 5K on the cross country trail and a family friendly 1 Mile fun run. Medals for all and shirts for early registrants add holiday cheer.

Join the Inwood Hill Turkey Trot, a festive Thanksgiving 5k through scenic Inwood Hill Park in northern Manhattan. Enjoy a family friendly run while supporting the Inwood Food Pantry and celebrating community spirit.

Run a scenic 5K at Bethpage State Park with the Never Stop Running Foundation Leftover Turkey Trot, offering in person and virtual options. Free kiddie dash with ribbons and proceeds support the foundation.