Naples
Trail Running Calendar near Naples 2026-2027
Explore the top trail runs near Naples for 2026-2027! We've gathered 18 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
A Halloween-themed 5K on the Lehigh Valley Trail in Mendon, NY with in-person and virtual options, a costume contest, prizes, and a post race brew.
Two 5K trail races at Ganondagan State Historic Site in Victor NY with a canicross class and a dog friendly 5K, timed results, 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.
A six-hour looped ultra at Finger Lakes Community College on November 14, 2026, raising funds for Shortsville's free dog park; dogs allowed on short leash.
January 2027
Winter trail run at Harriet Hollister Spencer State Recreation Area on January 9, 2027, an approximately 10k loop and the first race of the Common Ground Winter Trail Series.
March 2027
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 roughly 45 mile trail ultra in Letchworth State Park using both sides of the gorge, mostly off road, with six aid stations and stretches up to eight miles between them.
A free, self supported hill climb challenge in Naples NY where participants complete marked loops, log times with GPS, and compare combined results at Engine 14 Brewery.
August 2027
Mountain trail race at Swain Ski Resort of about 6.5 miles and 2,500 ft gain, a 2027 USATF Niagara championship event with climb and descent prizes.
September 2027
Trail races at Gannett Hill in Ontario County Park featuring a half marathon and a short course, on-course aid stations, post-race food and volunteer-supported parking.
Timed running options on a one mile grass and trail loop at Shortsville Reindeer Farm with barn aid, manual lap marking, and buckles for 100 loops.