Trail Running calendar near Naples 2025-2026

Join the 0 Degree Winter Trail Festival in Pittsford NY on Dec 13 for a chilly day of trail racing to raise funds for local trail projects. Choose 15, 10 or 5 mile courses that tackle the notorious Hell on Roots climb and Ski Hill Climb.

Tackle about 9 miles of scenic but often icy and technical trails in Highland Forest, Fabius, then enjoy an all you can eat pancake breakfast at Skyline Lodge. Shortcuts make this a fun, flexible winter outing for runners and families.

Brave snowy single track and winding trails at Harriet Hollister Spencer State Recreation Area in a scenic winter 10k loop. Bring traction friendly shoes and water, then warm up and unwind with fellow runners at a nearby brewery after the r..

Run winter trails at Ontario County Park on a roughly 4 mile loop with 4, 8 or 12 mile options and likely snow, so bring traction footwear. Warm up at heated Wilson Lodge with pancakes, hot drinks and post race snacks.

Embrace winter trails at Mendon Ponds Park on January 31, 2026 at Devil's Shadow Winter Trail Races, with 5 mile, new 25k, and 50k looped courses around the Devil's Bathtub. Cozy lodge aid station and friendly series vibes for all paces.

Enjoy a chip timed 5K through vineyard and orchard trails at Three Brothers Wineries in Geneva, NY. Celebrate at the finish with cider, a homemade donut and a medal in a fun family friendly race.

English's Ridge Rumble returns April 18, 2026 at Green Lakes State Park. Choose 50 km, 20 Miler, or 10 Miler on a scenic, technical loop with roots, rocks and roughly 1,300 feet of climb. USATF sanctioned.

Tackle rugged ski slopes at Buffalo Ski Center in Colden, NY with 50k or 100k options on a 10k loop featuring big climbs, unlit night sections and mandatory headlamps. Big finisher medals and unique awards make this a memorable challenge.

Push your limits on scenic single track around Hills Creek Lake with 3, 6 and 12 hour time based options plus a 12 hour four person relay. Run as many roughly 3 mile laps with about 200 ft of climb per lap and enjoy lakeside aid and camping..

Join the 19th Annual Medved Madness Trail Races on May 3, 2026 at Mendon Ponds Park in Honeoye Falls NY for scenic trail running. Choose about 13 mile or 5 mile courses or a kids run, then relax with a post race barbecue and a technical shi..

Run Letchworth State Park's dramatic gorge at the Sehgahunda weekend, with distances from 5K and relays to a two day 72K. Cup free aid stations, post race food, event shirts and unique finisher items await.

Sand to Serengeti offers scenic trail runs at Green Lakes State Park, starting on the sandy beach and climbing to the Serengeti high section. Run 10 miles or 3 miles and support Safe Space Organization's peer to peer mental health work.

Run among the waterfalls at Letchworth State Park on May 17 with 5K, 10K, or 15K routes starting and finishing at the Parade Grounds. Enjoy hilly, scenic out and back courses with sweeping Genesee River views and post race refreshments.

Run Cayuga Trails on May 30, 2026, through Ithaca gorges, waterfalls and historic stone stairs with wild singletrack underfoot. Choose a 50 mile or 50K challenge for a scenic, rugged ultramarathon experience.

Lucifer's Crossing at Robert Treman State Park in Ithaca is a scenic, rugged trail race through forest, gorge and historic stone stairs. Choose 5K, 10K or half for a challenging run with post race food and shirts for early registrants.

Hit the trails at Frost Town Trail Fest in Naples NY on June 6, 2026 with 25k and 10k races plus a 3k fun run for kids. Scenic Bristol Hills routes, aid stations, and proceeds support environmental education at Cumming Nature Center.

Join YMCA Race Weekend at scenic Green Lakes State Park for multisport and trail races including triathlon, aquabike, 8K and kids fun run. Compete, enjoy the lakefront trails and support YMCA programs that help the community.

Run Many On The Genny at Letchworth State Park on June 20, 2026, a scenic yet rugged 45 mile trail ultra with relay and women's only options. Gorge views, steep climbs, and grassroots aid stations await; registration opens January 1, 2026.

Join RHSC's Super Hear O 5K and Family Fun Day for a 5K run or one mile walk supporting communication for children with special needs. Family fun with free kids under 12 and team fundraising options.

Enjoy a scenic 5K through Sheldrake Point Winery vineyard with Cayuga Lake views, then relax with live music, a food truck and a complimentary glass for participants 21 and over. Finishers get a tech shirt and a souvenir stemless wine glass..