Naples
Trail Running Calendar near Naples 2026-2027
Explore the top trail runs near Naples for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Multi-day timed ultras at Shortsville Reindeer Farm on a one mile grass and trail loop. Multiple timed options, an on-course aid barn, and belt buckles for finishers who complete 100 loops; proceeds support ROCovery Fitness.
A memorial 5K run and walk at Mossy Bank Park in Bath NY, dogs welcome, $30 fee, with proceeds split between Mossy Bank and a local SPCA and additional funds to St. Jude.
October 2026
Trail festival near Hemlock, NY offering marathon, 15K and point to point 5K with technical single track sections and two major climbs.
Run a 5K through the private 157 acre Rochester Rotary Sunshine Camp on a mix of dirt trails and paved paths. Enjoy the post race Beer Fest and support accessible camping for children with disabilities.
Boos & Brews 5K in Mendon NY on 10/17/2026 offers a 3.1 miles in-person race and a virtual option, with a costume contest, awards and a post race party.
Canicross and dog-friendly 5K trail races at the Historic Ganondagan Site on October 17, 2026, with a vendor market, finisher medals, and age-group awards.
Hopson Trail Runs in Honeoye offers scenic fall trail routes of 5K and 9K through WoodsEdge Retreat and Sandy Bottom Park. The event supports Embrace Your Sisters and includes a post race gathering at Birdhouse Brewery with music and a complimentary..
A Halloween-themed team scavenger hunt run at DeWolfe Brewing in Victor on October 22, 2026, where teams complete checkpoints, post photos to earn points, and can earn bonus points.
November 2026
A 2.2 mile in-person and virtual challenge by EquiCenter to raise awareness of veteran and active military suicide and support local veteran programs.
Three-day trail stage race at Mendon Ponds Park featuring 3, 5.5, and 11 mile stages with timing and post-race food.
Run or walk as many loops as you choose during this 6 hour event on the Manchester Gateway Trail. This dog friendly race features a scenic 2.3 mile course and benefits the local dog park through a dedicated raffle.
January 2027
Winter trail race on Jan 2, 2027 at Harriet Hollister with an approximately 10k loop, no on-course aid, and a post-race gathering in Honeoye.
March 2027
A free morning group run on March 20, 2027 at Mendon Ponds Park with a 5 km hike option and a 10 km run, cake, informal surprises, and volunteer opportunities.
A chip timed 5K run and walk at Three Brothers Wineries and Estates in Geneva NY on March 27 2027 with a T shirt, cider pour, medal and donut.
June 2027
A 45 miles trail ultramarathon through both sides of Letchworth State Park with five aid stations and long remote sections.
A free GPS tracked hill-loop challenge around Naples, NY supporting the Naples Trail Collective with multiple named climbs and an honor system combined time result.