Trail Running Calendar New York 2025-2026

The Two Hollows Monster Marathon and Half Marathon takes place in the scenic Kennedy State Forest near Virgil, NY, featuring well-maintained trails between Daisy Hollow and Babcock Hollow. The course offers rolling single-track paths, challenging hills, and shaded hemlock and hardwood forests, with..

The Thacher Park Trail Running Festival, held annually at Thacher State Park in Voorheesville, NY, offers a scenic and challenging trail running experience. Participants can choose from four distances: 10K, half marathon (13.1 miles), marathon (26.2 miles), and an ultra 50K. The course features a sh..

Raptor Ridge, presented by Peace, Love, Trails (formerly Sanctuary 6.5), is a 6.5-mile trail race through Westmoreland Sanctuary in Westchester County, NY. The route runs over challenging trails within the nature preserve (spanning Bedford, Mount Kisco and Armonk). The race starts and finishes at Fo..

The Black Diamond Express Races take place on the Lehigh Valley Trail in Mendon, New York, offering a 5K and a Half Marathon along a rails-to-trails route. The Half Marathon is USATF-certified (NY17052JG) and part of the Greater Rochester Track Club’s Rochester Runner of the Year Series; the course..

The Bread of Life Outreach Center Wellness Day 5K Trail Run takes place at Sprague Brook County Park in Glenwood, New York. Scheduled for September 6, 2025, the event features a 5K trail run on wide, groomed trails and grass, as well as a 2-mile non-timed trail walk option. The start and finish are..

The Glen Iris 5K & 10K Trail Run/Walk is a scenic event held within Letchworth State Park, known as the "Grand Canyon of the East," in Castile, NY. Participants will enjoy challenging woodland trails with breathtaking views of the Genesee River Gorge, wildlife, streams, and bridges. The race feature..

Located at Lakeside Park in Pawling, New York, the Pawling 24 Hour Trail Running Festival is the sixth edition of the endurance event, offering 24-, 12-, 6-, and 3-hour races (including a 12-hour night start). Runners tackle a 1.68-mile loop made up of pavement, grass, and single-track, with about 1..

Virgil Crest Ultras is a multi-distance ultramarathon in Cortland, New York, offering a 100-mile, 50-mile, and 50K. Known for its tough terrain—Aint Easy—with steep ascents and descents, large cumulative gain and loss, and variable weather. The course opens with a sunrise climb through forest single..

Ontario Summit Trail Races, celebrating its 10th anniversary, take place at Ontario County Park at Gannett Hill in Naples, NY. The event offers a Half Marathon (13.1 miles, one-way, mostly single-track around the summit) and a 5 Mile race that stays within the park with gentler elevation. Expect roc..

The ESM Open XC Race 2025 is a 5K cross-country running event held at Pine Grove Middle School in East Syracuse, New York. The race takes place on the school's varsity cross-country course, offering a competitive and scenic route for runners of all levels. Open to all participants, the event encoura..

Wilcox Wild is a challenging 50K trail ultra run held in the Adirondack Park Wilderness, New York, on September 13, 2025. The race features a rugged lollipop course starting and finishing at Harrisburg Lake, covering 31 miles with 3,028 feet of elevation gain and loss. Runners traverse scenic trails..

The Mill to Mill 5K/10K (Keuka Outlet Trail) is an annual running event held in Penn Yan, New York, starting and finishing at Cascade Falls along the scenic Keuka Outlet Trail. The race offers two distances: a 5K and a 10K. Both courses pass by the picturesque Seneca Mills Falls, with the 10K extend..

Shawangunk Ridge Trail Run (SRT) unfolds along the Shawangunk Ridge in the Hudson Valley, offering three divisions: 70-mile, 30-mile, and 1/2 marathon, spanning from High Point Monument in NJ to Rosendale, NY. The route winds through hills, wetlands, pine barrens, sky lakes, waterfalls, and conglome..

The Clover Dash 5K is a trail race in Canandaigua, New York, benefiting 4-H Camp Bristol Hills as it marks its 100th anniversary. The event offers a 5-kilometer trail distance and features the Clover Dash 100 Minute Challenge. The course is located at 4437 Kear Road, Canandaigua, NY 14424.This commu..

Brookfield Classic takes place in Brookfield, New York, deep in the woods of the Charles E. Baker State Forest. The event features three trail distances: 5K, 15K, and a 50K Ultra Marathon.The 5K offers a beginner-friendly option to ease into trail running. The 15K traverses a loop over a mix of truc..

The ROCovery Fitness Annual Run/Walk & X-Challenge is held in Henrietta, NY, at Mendon Ponds Park. This event celebrates fitness and recovery during National Recovery Awareness Month and supports individuals recovering from alcohol and substance use disorders. Participants can choose from multiple o..

The Sleigh Me 24 and 48 Hour Ultra is an endurance running event held at the Shortsville Reindeer Farm in Shortsville, NY. Participants run loops of a one-mile course featuring grass and trail terrain with minimal elevation, surrounded by reindeer, chickens, honey bees, and maple trees. Runners can..

The Champlain Bridge 5K and 2 Mile Fun Run/Walk is a family-friendly event held at Crown Point State Historic Site and DEC Campsite in Crown Point, New York. The scenic 5K cross-country course winds through trails, roads, and fields, symbolizing hope and connection through the lighthouse and bridge..

Broken Cabin 10k is a 10-kilometer trail race held near Batavia, New York. In its second year, the event takes place on a privately owned trail system made possible by generous landowners. The course blends challenging segments with scenic beauty, and is designed for runners of all levels, offering..

Morgan Hill Trail Races take place in Morgan Hill State Forest, Fabius, New York. The lineup includes Hill to Hollow 100km, a 100km relay, the Morgan Hill Meat Grinder Marathon, and the Morgan Hill Half Marathon. Courses run mainly on the Onondaga Trail, with single-track terrain along misty ponds,..