Trail Running calendar near Canandaigua 2025-2026

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 Step Outdoors TRYathlon & 5K Trail Run/Walk takes place at Hills Creek State Park in Wellsboro, Pennsylvania. Participants can choose to compete solo in the TRYathlon, join a team, or participate in the 5K Trail Run/Walk. The TRYathlon consists of three legs: running or walking a course around H..

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..

Hill to Hollow 100km is the inaugural trail race in central New York, crossing four counties with start and finish in Morgan Hill State Forest near Tully. The ~63.7-mile course climbs about 10,286 feet and traces the Onondaga Trail and the North Country Trail east to Highland Forest, then winds via..

Aw, Schugs 100 & 30hr is a low-key ultramarathon held at Dryden Lake Park in Dryden, New York (W Lake Rd, Dryden NY 13053). The event offers two options on the same course: a 100-mile finish and a 30-hour time format. Runners follow a looping course that starts at the park pavilion, with each full l..

Morgan Hill Trail Races take place at Morgan Hill State Forest in Fabius, NY, offering 100km, a 100km relay, the Meat Grinder Marathon, a Half Marathon, and a Half Marathon Hike. The courses run mostly on the Onondaga Trail, featuring misty ponds, spectacular vistas, waterfalls, and fall colors, inc..

Parallel of Latitude Endurance Race is an 8-hour fixed-time event in Dryden, New York, at Dryden Lake Park. Runners tackle a flat, 3.45-mile out-and-back rail-trail loop beside Dryden Lake, with relay options for 2–6 participants. The course is described as low-key and flat, welcoming all paces and..

This 3.1-mile benefit run/walk takes place in Wellsboro, Pennsylvania, on Saturday, September 27, 2025. The course starts and ends at Stony Fork Campground and features grass, gravel, and dirt trails with two creek crossings, so participants may get their feet wet. Proceeds benefit the Chromosome 18..

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. This scenic race offers participants a unique trail experience with aid stations sponsored by Tailwind and encourages runners to b..

Time For A Wine Run at Spring Lake Winery is a trail race held in Lockport, New York, on the Spring Lake Winery property. Runners choose between a 2.5-mile single-loop or a 5-mile double-loop course, both mapped along groomed winery trails. The post-race scene unfolds in the Wine Garden, featuring s..

The Great Swamp Conservency 5k Trail Run is a scenic trail race held in Canastota, New York, within the boundaries of the Great Swamp Conservency habitat center. The 5-kilometer course features natural trails and crosses a country road, offering participants a chance to experience the area's unique..

The PYO Glow Run is a family-friendly 5K glow-in-the-dark fundraiser held in Athens, Pennsylvania, at Athens Valley Playland (2 South River Street). The event takes place on Saturday, October 11, 2025. Participants can run or walk the illuminated course, with a Spirit Walk option.The route follows t..

Rob's Trail Fest is a fall trail-running event in Hemlock, NY, at the south end of Canadice Lake, on Oct 11, 2025. It features three distances: Marathon, 15K, and 5K. The course mixes single-track, gravel, and a small amount of paved surfaces, including two 800-foot climbs on the marathon and a fast..

The Ives Run Trail Challenge is a 4-mile trail race held at the Ives Run Recreation Area in Tioga, Pennsylvania. The course features varied terrain, offering a technical yet approachable route for runners of different abilities. This annual event occurs on Saturday, October 11, 2025, at the Stephenh..

Green Monster Trail Challenge in Wellsboro, PA, in the Tioga State Forest north of PA Grand Canyon, offers 15K, 25K and 50K options for runners and hikers. The course features rolling single-track, steep ascents, numerous stream crossings and technical descents through rugged mountain terrain. Eleva..

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 by benefiting a fully accessible summer camp on 157 private acres. The course features a mix of paved sidewalks..

Hopson Trail Runs - Give Cancer The Bird unfolds in Honeoye, New York, offering a 5K Run/Walk and a 9K Run—the only 9K in New York—timed by Robinhood Racing. Set along wide grassy trails through WoodsEdge Retreat and established paths in Sandy Bottom Park, the course is vehicle-free and framed by fa..

Many Lite in Castile, NY, is a Trails Roc and Rochester Running Company collaboration held at Letchworth State Park—the Grand Canyon of the East. The event offers a 20-mile run and a 20-mile hike along a gorge-lined course featuring waterfalls, overlooks, and peak fall foliage along the Genesee Rive..

The Hunt Hollow Colorfest 5K is a unique and challenging mountain run held in Naples, New York, hosted by the Hunt Hollow Ski Club in partnership with Medved. The course features significant elevation gains and losses, offering a distinctive experience for runners, walkers, and hikers of all levels...