Trail Running Calendar New York 2025-2026

Trail run on snowy forest paths and an all you can eat pancake breakfast at Skyline Lodge in Highland Forest on Dec 20. Choose the full 9 mile course or take marked shortcuts and run at your own pace through rugged scenery.

Brave snowy single track and winding trails at Harriet Hollister Spencer State Recreation Area in a scenic winter 10k loop. Bring traction friendly shoes and water, then warm up and unwind with fellow runners at a nearby brewery after the r..

Run winter trails at Ontario County Park on a roughly 4 mile loop with 4, 8 or 12 mile options and likely snow, so bring traction footwear. Warm up at heated Wilson Lodge with pancakes, hot drinks and post race snacks.

Join Pond Fest Winter Trail Runs and Snowshoe at Chenango Valley State Park during the Pond Festival for scenic looped trails from 10k to 50k and a kids race. Crowds and aid at the start and finish make for a lively, supportive day.

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

Shake off winter with the Old Man Winter Trail Race at Marjim Manor, a scenic 3.2 miles through winery grounds and apple orchards on January 24, 2026. Register by Jan 16 for a special embroidered hat, chip timing, finish photos, and awards.

The Stone Wall is a snowshoe race in Winona on January 25 offering 5K family friendly and 10K challenging forest courses. Expect wooded trails, stone walls, creeks and steep terrain, plus post race refreshments and limited loaner snowshoes.

Embrace winter trails at Mendon Ponds Park on January 31, 2026 at Devil's Shadow Winter Trail Races, with 5 mile, new 25k, and 50k looped courses around the Devil's Bathtub. Cozy lodge aid station and friendly series vibes for all paces.

Fire and Ice Winter Run, Feb 21 2026 at Gilbert Lake State Park, offers 50k, 25k and 10k on scenic looped trails and is snowshoe friendly. Warm aid, a finisher mug, special awards and proceeds benefit The Neighborhood Center.

Shake off winter on Feb 22, 2026 at the Cabin Fever Trail Races in Webster Park, NY with 5 miles or 10 miles through scenic trail loops. Packet pickup Saturday is recommended and there are overall and age group awards.

Run along Lake Ontario to Tibbetts Point Lighthouse at the DENFIT Winter Soldier on Feb 28, 2026. Choose 10k, half, or a capped 100 person full marathon and enjoy fireside camaraderie, warm showers, medals and a new SPEAR finisher award.

Run the 4 Leaf Clover 5K at Bethpage State Park on March 8, 2026. Enjoy scenic soft trails, a free kiddie Clover run and a one week virtual 5K, plus a themed shirt while supporting the Never Stop Running Foundation.

Run or walk a chip timed 5k through scenic vineyard trails at Osprey’s Dominion Vineyards in Peconic, NY. Finish with a finisher medal that doubles as a wine stopper, a keepsake wine glass and a post race pour for eligible participants.

Tackle technical, rugged trails and steep climbs at Big Bear Squatch North in Bear Mountain NY on April 4, 2026. Choose a challenging 10K or a grueling half marathon, with proceeds supporting the New York New Jersey Trail Conference.

Enjoy a chip timed 5K through vineyards and orchards at Three Brothers Wineries, with cider, a cider donut and a finisher medal. Walkers, kids and strollers welcome for a fun family outing supporting Geneva Community Projects.

Join the Bunny Trail 5K at Bethpage State Park for a family friendly run starting on a grassy polo field and winding onto scenic soft trails. In person and virtual entries plus a free kiddie run support the Never Stop Running Foundation.

Join Run for the Rescue on April 11, 2026 for a scenic 5K through Blydenburgh County Park with on site and virtual options. Tackle varied trails, enjoy post race refreshments, and support Last Chance Animal Rescue.

Join the John Jay Community Trail Race in Cross River NY on Sunday April 12, 2026 for a family friendly outing with a 5k, 4k Jay Walk and a 200 meter Kids Dash. Race on scenic wooded, hilly school trails and finish at the track.

English's Ridge Rumble returns April 18, 2026 at Green Lakes State Park. Choose 50 km, 20 Miler, or 10 Miler on a scenic, technical loop with roots, rocks and roughly 1,300 feet of climb. USATF sanctioned.

Run the scenic Shore2Shore trail event from Sunken Meadow to Heckscher State Park on Apr 18, 2026, with 25K and 50K options along the Long Island Greenbelt Trail. Well stocked aid stations, shuttle service and a logo shirt make for a memora..