Trail Running calendar near Canandaigua 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 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 Pine Creek Challenge is a scenic trail ultramarathon held in Wellsboro, Pennsylvania, offering 100 Miler, 100K, 50 Miler, and Marathon distances. The out-and-back course uses 25 miles of the upper Canyon section through the Pine Creek Gorge, the Grand Canyon of the East and a National Natural La..

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..

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..

Sugarbush Shenanigans is an ultrarunning event held at Sugarbush Vineyards & Winery in Hillier, Ontario, Canada. Part of the OUTRace Series, it offers 6, 12, and 24-hour solo ultra-marathon options, as well as a 24-hour relay team race. A new 12-hour night run starting at 9 PM is also available.The..

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..

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..

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..

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..

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,..

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..

Brayden's Benefit 5k Run/Walk takes place in Wellsboro, Pennsylvania, starting and finishing at 658 Stony Fork Creek Rd at the Stony Fork Campground. The 3.1-mile course winds through grass, gravel, and dirt trails and includes two creek crossings, so participants may get their feet wet. Proceeds be..

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..

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..