Trail Running calendar near Naples 2025-2026

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..

Glen Iris 5K & 10K Trail Run/Walk takes place in Letchworth State Park, Castile, NY, known as the Grand Canyon of the East. Both woodland-trail courses start and finish near Trout Pond, offering challenging routes with forest views, creeks, bridges, and wildlife. The event provides a social, scenic..

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..

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..

Located in Morgan Hill State Forest, Fabius, NY, the Morgan Hill Trail Races offer several distances: 100km, 100km Relay, a marathon, half marathon, and half marathon hike. The mostly single-track Onondaga Trail threads through misty ponds, striking vistas, and waterfalls, with the marathon adding F..

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..

The Marilla Trail Race, held at Marilla Reservoir in Bradford, Pennsylvania, offers trail running events of 14 miles and 7 miles, along with a 4-mile hike. Set amid rolling hills and dense forests, the race features clearly marked trails including gravel paths, dirt trails, and winding single track...

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..

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..