Trail Running calendar near Middlesex 2025-2026

The Pine Creek Challenge is a scenic trail running event held in Wellsboro, Pennsylvania, featuring distances of 100 miles, 100K, 50 miles, and a marathon. The course follows the Pine Creek Rail Trail, a 63-mile crushed stone path through the Pine Creek Gorge, known as the "Grand Canyon of the East...

The Bread of Life Outreach Center Wellness Day 5K Trail Run is held at Sprague Brook County Park in Glenwood, New York. This event features an approximately 5K trail run/walk on wide groomed trails and grass, starting and finishing near the park's Warming Shelter. Participants registering by August..

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..

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..

The Broken Cabin 10k is a trail running event held just outside Batavia, NY, on a privately owned trail system suitable for runners of all levels. This inaugural race aims to create a friendly, backyard race atmosphere that emphasizes fun and quality. The course offers a welcoming environment for pa..

The Ontario Summit Trail Races, held at Ontario County Park at Gannett Hill in Naples, NY, offer a scenic trail running experience featuring a half marathon and a 5-mile race. The half marathon covers 13.1 miles of rolling, tree-covered single-track trails around Gannett Hill, the highest point in O..

The Virgil Crest Ultras, held in Cortland, New York, is a challenging trail running event featuring distances of 100 miles, 50 miles, and 50 kilometers. Known for its significant ascents and descents, the course offers steep climbs, singletrack forest trails, and less technical footing that allows r..

The ROCovery Fitness Annual Run/Walk & X-Challenge takes place in Henrietta, NY, at Mendon Ponds Park. This event, held in September to honor National Recovery Awareness Month, offers multiple race options including a 5k road course, 5k trail course, a 5k trail with an X-Challenge, a virtual 5k, and..

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 Parallel of Latitude Endurance Race is an 8-hour fixed-time running event held at Dryden Lake Park near Dryden, NY. Participants run a flat, scenic 3.45-mile out-and-back course along a rail trail beside Dryden Lake. The race welcomes all paces, including walkers, with no mileage or time cutoffs..

The Unlimited Breadsticks Trail Race Half Marathon is a 13-mile trail running event held in Victor, New York, starting at Parkview Fairways and finishing near Valentown. Scheduled for Sunday, September 28, 2025, this race offers a unique trail experience capped at 200 participants. Runners enjoy aid..

Rob's Trail Fest, held in Hemlock, NY, is a trail running event featuring marathon, 15K, and 5K distances. Scheduled for October 11, 2025, the festival offers runners scenic courses showcasing stunning fall foliage. The marathon includes two challenging technical climbs of 800 feet each on single-tr..

The HoliTrot Fall Festival Trail Run is an annual event held at HoliMont, America's largest private ski resort located in Ellicottville, New York. This festival features a kids' race alongside a 5K trail run, offering a family-friendly atmosphere that celebrates outdoor fitness and community spirit...

The Green Monster Trail Challenge is a demanding trail running and hiking event held in the scenic Tioga State Forest near Wellsboro, Pennsylvania. Offering three distance options—15K, 25K, and a challenging 50K—the course features rugged terrain with steep climbs (up to 7,800 feet total ascent for..

The Sunshine Camp Trail Mix & Beer Fest is an annual 5K trail race held at Rochester Rotary Sunshine Camp in Rush, New York. This event supports children and young adults with disabilities who attend the fully accessible summer camp. The course features a mix of paved sidewalks and natural dirt trai..

Nocturnal 12 is a 12-hour fixed-time endurance race held in Rochester, New York, along the paved Lake Ontario State Parkway Trail between Island Cottage Road and Dewey Avenue. Participants can walk or run as many 2.06-mile out-and-back laps as they wish within the 12-hour window, making it walker an..

Many Lite is a scenic 20-mile running and hiking event held in Castile, NY, within the stunning Letchworth State Park, often called the Grand Canyon of the East. The course features breathtaking views of waterfalls, overlooks, and vibrant fall foliage along the Genesee River gorge, with cliffs reach..

The Run For Your Life 5k in Batavia, NY, is a unique nighttime race combining a 5k run with a haunted house experience. Held in complete darkness, participants must wear headlamps as they navigate a spooky course featuring classic horror characters who create a thrilling atmosphere without physical..

The Dirt Cheap Stage Race is a challenging three-day trail running event held at Mendon Ponds Park in New York. It features three stages: a 3-mile time trial on Pond Road, a 5.5-mile trail run finishing with a notorious stair climb at Devil's Bathtub, and an 11-mile epic trail run through the park's..

The 0 Degree Winter Trail Festival is a trail running event held in Pittsford, New York, featuring three race distances: 15 miles, 10 miles, and 5 miles. The festival serves as a fundraiser to support various trail projects in the area. The course includes challenging features such as the "Hell on R..