Trail Running Calendar New York 2025-2026

Take on a crisp late November trail at Stillwell Woods Preserve in Woodbury on November 30, 2025. Rob's Trail Run Edition features a scenic 5K with separate adult and high school youth divisions for runners of all levels.

Run or walk the Never Stop Running Foundation Turkey Trot, a scenic trail 5K at Belmont Lake State Park on November 30, 2025, supporting a great cause. Enjoy post race refreshments and a 50 50 raffle with proceeds benefiting the foundation.

Get festive at the Ugly Sweater 5K in Canajoharie on December 6, 2025, where runners and walkers hit the scenic Erie Canal trail in holiday style. All proceeds support the Community Youth Center and age group prizes add extra fun for racers..

Run a timed 50 miles or 50 kilometers in Prospect Park on a scenic looped course near Lincoln Road. Community aid with Skratch Labs hydration and a potluck style aid station keeps you fueled across the day.

Tough Cookie 8K at Sunken Meadow State Park offers scenic cliffside views of the Long Island Sound, festive cookie stops and a post race cookie fest. All paces welcome and proceeds support local charities.

Tackle rugged trails and steep climbs at the 0 Degree Winter Trail Festival in Pittsford, NY, a fundraiser supporting local trail projects. Choose 5, 10 or 15 mile routes for a cold season trail challenge with grit and scenic views.

Run until only one remains at SRC Presents: A Backyard Ultra in Blydenburgh County Park on December 13 and 14, 2025, looping a rugged 4.167 mile trail. Day and night loops, limited crew access, and proceeds support the Long Island Greenbelt..

Tackle about 9 miles of scenic but often icy and technical trails in Highland Forest, Fabius, then enjoy an all you can eat pancake breakfast at Skyline Lodge. Shortcuts make this a fun, flexible winter outing for runners and families.

Start the season with Frozen Assets, a scenic 10k winter trail loop at Harriet Hollister Spencer State Recreation Area that often runs through snow. Carry your own water and enjoy warm cider at the finish.

Take on a crisp winter trail at Gannett Hill in Naples, NY with 4, 8 or 12 mile options around a scenic 4 mile loop. Warm up afterward in the heated lodge with pancakes, hot drinks and a cozy fireside finish.

Enjoy winter trail runs and a snowshoe race at Chenango Valley State Park during the Binghamton Pond Festival, with festival vibes near the start. Choose 10k, 20k or 50k loops or a free kids run and support local youth programs.

The Gurney Lane 5K Snowshoe Race will take place in Queensbury on Saturday 17 January 2026. You can run 5 kilometers.

Old Man Winter Trail Race at Marjim Manor in Appleton NY on Jan 24, 2026 invites runners to a scenic 3.2 mile loop through orchard and farm trails. Register early for an embroidered hat and enjoy chip timing and on site race gifts.

The The Stone Wall Snowshoe Event will take place in Mannsville on Sunday 25 January 2026. You can run between 5 and 10 kilometers.

Run Devil's Shadow Winter Trail Races at Mendon Ponds Park on January 31 2026 with 50k 25k and 5 mile loops around the Devil's Bathtub. Hopkins Point Lodge provides a warm aid station and post race treats while Common Ground Series swag awa..

Try the Fire and Ice Winter Run at Gilbert Lake State Park for scenic snowy loops on forest, gravel and road with options for 10K, 25K or 50K and snowshoes welcome. Warm aid, coffee and fireplaces at the Briggs cabin and proceeds support a..

Join DENFIT Winter Soldier on Feb 28 in Cape Vincent for a flat out and back run to Tibbetts Point, with marathon, half and 10k distances. Finishers receive a shirt and medal, full marathoners the DENFIT SPEAR, plus showers, music and a fir..

Run the Never Stop Running Foundation 4 Leaf Clover 5K at Bethpage State Park on March 8 2026 for a scenic trail 5K across grassy polo fields and winding soft trails. Family friendly with a kids run, virtual race and refreshments.

Enjoy a scenic 5K around Osprey's Dominion Vineyards in Peconic, NY on a two lap cross country style course for runners and walkers. Finishers get a shirt, bottle stopper medal, shatterproof wine glass and a wine pour.

Run rugged trails at Big Bear Squatch North in Harriman State Park on April 4, 2026 with half marathon, 10K and ruck divisions. Expect steep climbs, scrambling terrain and sweeping Hudson Valley and NYC skyline views.