Trail Running Calendar New York 2026-2027

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.

Join a scenic 6K snowshoe at Natural Stone Bridge and Caves on Jan 24, 2026, with rugged forest trails, caves and mountain views. Part of the DION WMAC series with timing, prizes and limited loaner snowshoes plus a warming bonfire.

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.

Experience a winter trail challenge on January 31, 2026 at Mendon Ponds Park, with a scenic loop around Devil's Bathtub and warm aid station comforts at Hopkins Point Lodge. Choose from 50k, 25k or 5 mile options as part of the Common Groun..

Beast of Burden Winter is a chilly ultramarathon in Lockport, NY with 25, 50 and 100 mile options on February 7, 2026. Run the scenic Erie Canal towpath where snow is possible and enjoy warming shelters and hot aid station fare.

A late-winter trail run at Gilbert Lake State Park offering 50K, 25K, and 10K on a marked 6-mile loop with aid at a lakeside cabin and proceeds supporting The Neighborhood Center.

Cabin Fever Trail Races in Webster Park on February 22, 2026 feature approximately 5 and 10 mile winter trail courses through pine woods, a long sleeve shirt for early registrants, post-race food, and age-group awards.

Run a flat, fast course from Cape Vincent Recreation Park to Tibbetts Point Lighthouse on Feb 28, 2026, with 10k, half and full marathon options. Enjoy post race warmth, music and medals, with a new DENFIT SPEAR for full marathon finishers.

Join the Frigus Snowshoe Festival at Moreau Lake State Park for fun snowshoe races from a kids mile to a 60K on scenic winter trails. Snowshoes are required and all finishers get medals while top racers earn awards.

Join the Never Stop Running Foundation 4 Leaf Clover 5K at Bethpage State Park, a scenic trail run starting on a grassy polo field. Family friendly with a kiddie fun run, virtual 5K and post race refreshments supporting the foundation.

The Ospreys Dominion Wine Run 5K will take place in North Fork on Saturday 21 March 2026. You can run 5 kilometers.

Tackle a rugged, technical 10k through Van Cortlandt Park in the Bronx on March 29, 2026, and grab a commemorative souvenir. A portion of entry fees supports the Van Cortlandt Park Alliance for trail upkeep and youth programs.

Run rugged, technical trails at Bear Mountain with 10K or half marathon options and stunning Hudson Valley and NYC skyline views. Proceeds support the New York New Jersey Trail Conference; race day is Apr 4.

Run or walk a chip timed 5K through scenic vineyards and orchards at Three Brothers Wineries and Estates. Enjoy a cider donut, shirt and a finisher medal that doubles as a bottle opener, with family friendly and virtual options.

Run the Bunny Trail 5K at Bethpage State Park for a scenic start on the polo field and winding soft trails with a cross country feel. Family friendly with free kiddie run and virtual option, benefiting the Never Stop Running Foundation.

Run a scenic 5K through trails and vineyards at Spring Lake Winery in Lockport on April 4, 2026. Enjoy finish line snacks, a keepsake wine glass, and post race food and drinks with live music and festivities.

Join Last Chance's Run for the Rescue, a scenic 5K at Blydenburgh Park on April 11 with virtual entry through Apr 19. Bring leashed dogs, enjoy trails and refreshments, and support Last Chance Animal Rescue.

A USATF certified point to point half marathon in Albany County on April 11, 2026, mostly on paved rail trail with a net downhill and a 500 foot elevation drop to a Hudson River finish. The event offers live tracking, bus to the start, post..

Run or walk the John Jay Community Trail Race in Cross River through scenic wooded trails and rolling hills, with 5k, 4k walk and a Kids Jay Dash on the track. A family friendly community event that finishes on the John Jay Contest Field.

English's Ridge Rumble at Green Lakes State Park in Fayetteville NY offers 50 km, 20 mile and 10 mile trail distances. Run varied trails around the park's striking blue green meromictic lakes for a scenic and challenging mid April outing.