Trail Running calendar near Naples 2026-2027

Experience the trails of Highland Forest County Park with 10 mile, 20 mile, and 50K distance options. This event features technical terrain and significant elevation gain through forests and logging lanes near Fabius.

The Mills Miles is a Last Runner Standing event at Powder Mills Park in Pittsford, NY featuring repeated one mile loops with time cutoffs, a final all out lap, post-race BBQ and awards, and fundraising support for TrailsROC.

A single-day endurance walk at Holiday Valley, Ellicottville on May 24, 2026, offering 7, 14, 21, or 28-mile options with optional 10/20/35 lb rucking, a 10-hour finish window, well-marked trails, and regular aid stations.

A budget-friendly midweek trail series across four Monroe County parks offering single-race entries or an all four series option. Features chip timing, a post-race cookout, series scoring and awards plus a custom hat for series entrants.

Cayuga Trails in Ithaca, NY is a primarily singletrack race featuring waterfalls, stone stairs, and two distances, a 50 mile and a 50K. The race has a 440 runner cap, drop bag service, post-race gear, and charity support.

Trail running in Ithaca, NY with a Half Marathon, a 6.66 Miler and a 5K on park trails. The looped course uses the Rim Trail, Gorge Trail, Red Pine and Finger Lakes Trail and includes park entry, a shirt and post race food.

A four-week, 90-minute trail running series for runners comfortable with about 3 miles. Sessions cover warm-ups, guided runs, hill and footwork drills, gear and safety, and include trail socks and gifts.

Trail runs in Naples NY with a rugged 25K single loop around the Cumming Nature Center and Honeoye Inlet Wildlife Management Area and a more runnable 10K. Proceeds support environmental education at the RMSC Cumming Nature Center.

A farm-based ultrarun on 06/06/2026 at Fish's Farm Market in Shortsville, NY where participants run or walk as many 1.52-mile loops as they wish. Timing, aid station, medals, prizes and raffles; proceeds benefit Colony Caregivers.

Join an inclusive superhero themed event at Seneca Park featuring a 5K road run and a paved one mile walk. Celebrate the mission of the Rochester Hearing and Speech Center with family activities and ice cream for all participants.

Trail races at Mendon Ponds Park on a 4 mile loop with an 8 mile two loop option. The course is off road with about 350 ft of elevation gain per loop and requires runners to carry their own fluids.

A two-day event at Green Lakes State Park with Saturday swim-bike-run races and Sunday trail and kids runs. Registration opens July 21, 2025 and fees vary by event.

Run with a View V is a 5K trail race at Mt. Pisgah County Park in Troy, PA on June 13, 2026. The course follows wooded paths with rocks, tree roots and some hills and is not stroller friendly; registration closes May 28.

A Last One Standing loop race at Clark Reservation State Park in Jamesville, NY, featuring two short circuits over table rock and mixed trail. Cutoff times shrink each lap and the event concludes with a post-race cookout.

A 45 mile all trail ultra in Letchworth State Park that follows both sides of the gorge. It includes a relay option and multiple aid stations with remote stretches between stations.

A mud obstacle trail run at Holiday Valley in Ellicottville, NY with 15 obstacles and three course options including a kids race. Courses follow the ridgeline past Spruce Lake and all finishers receive medals.

A self-timed family run and walk at Tap Root Fields with mapped loops through fields and wood-chipped trails, picnic areas, a bounce house, and strawberry-themed refreshments. Open to all ages; pets are not allowed.

Explore the scenic trails of Monroe County during this four part mid week race series. Enjoy chip timed runs through various local parks along with post race cookouts and custom series participant awards.

A chip timed 5K through Sheldrake Point Winery with vineyard trails and Cayuga Lake views, a tech shirt and stemless wine glass for participants, age based awards, and a complimentary glass of wine for finishers 21 and over.

A trail race at Buttermilk Falls State Park featuring a 10K plus course with varied terrain, a steep climb and fast downhill finish, plus a free untimed 1 mile kids fun run.