Trail Running calendar near Naples 2025-2026

We have found 28 Trailruns within 80 miles of Naples. See below where and when you can find the races.

Run or walk the Batavia Turkey Trot 5K on Thanksgiving Day and support Crossroads House. Family and stroller friendly with costume prizes, hot drinks and snacks after the race.

Celebrate Thanksgiving at the Gratitude Run held at Rochester Rotary Sunshine Camp with a family friendly 5K, 1 mile, kids dash and virtual options. Run scenic camp trails and support Sunshine Camp programs for children with disabilities.

December 2025

Tackle rugged trails and steep climbs at the 0 Degree Winter Trail Festival in Pittsford, NY, a fundraiser supporting local trail projects. Choose 5, 10 or 15 mile routes for a cold season trail challenge with grit and scenic views.

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.

January 2026

Start the season with Frozen Assets, a scenic 10k winter trail loop at Harriet Hollister Spencer State Recreation Area that often runs through snow. Carry your own water and enjoy warm cider at the finish.

Take on a crisp winter trail at Gannett Hill in Naples, NY with 4, 8 or 12 mile options around a scenic 4 mile loop. Warm up afterward in the heated lodge with pancakes, hot drinks and a cozy fireside finish.

Run Devil's Shadow Winter Trail Races at Mendon Ponds Park on January 31 2026 with 50k 25k and 5 mile loops around the Devil's Bathtub. Hopkins Point Lodge provides a warm aid station and post race treats while Common Ground Series swag awa..

April 2026

Run a festive 5K through vineyards and orchards at Three Brothers Spiked Apple in Geneva. Enjoy cider, a cider donut, a finisher medal and free finish line photos in a family friendly event open to all ages.

English's Ridge Rumble returns April 18, 2026 at Green Lakes State Park with 50 km, 20 mile and 10 mile options on scenic but challenging trails. Expect varied surfaces, technical sections, open fields, and about 1,300 ft of climbing.

UTMB Index
May 2026

Tackle rugged ski slopes at DENFIT ULTRA in Colden NY with 50k or 100k options on a challenging 10k loop. Expect notable climbs, possible snow and natural obstacles. Headlamps are required and basecamp tents, food and big finisher medals aw..

Medved Madness Trail Races at Mendon Ponds Park offer long and short courses plus a Kids K on scenic spring trails. Participants receive a gender specific tech shirt and are invited to a lively barbecue to celebrate the day.

Take on the rugged Sehgahunda Trail Marathon and relays at Letchworth State Park on May 16 with the Vale of Three Falls races on May 17. Expect technical singletrack, big climbs, handmade finisher medals and a true trail weekend.

Run the Sand to Serengeti at Green Lakes State Park and choose a scenic 10 mile beach to field route or a breezy 3 mile lake loop. Enjoy well marked trails, race day photos, finisher swag, and local community support.

Run the Vale of Three Falls at Letchworth State Park on May 17, 2026 with 5K, 10K or 15K routes that follow a scenic service road overlooking the Genesee River. Expect rugged terrain, big hills and post race refreshments.

Cayuga Trails in Ithaca NY on May 30 threads epic singletrack through gorges, waterfalls and historic stone stairs with big climbs. Pick a 50 mile or 50K route and enjoy stocked aid stations, drop bag support, local post race food and a fin..

Tackle scenic singletrack in Robert H Treman State Park at Lucifer's Crossing. Choose 5K, 10K or a half marathon with a rolling rim trail climb, gorge descents and historic stone staircase for challenging, unforgettable views.

June 2026

Join YMCA Race Weekend at scenic Green Lakes State Park June 13 to 14 for multisport races, an 8K trail run through forests and meadows, and a Kids Fun Run on the beach. Proceeds support YMCA community programs.

Take on Many On The Genny, a 45 mile trail ultra through Letchworth State Park's gorge with long climbs, footbridges and sweeping views. Solo, relay and women's only entries available; registration opens Jan 1, 2026.

Join RHSC's Super Hear O 5K & Family Fun Day at Seneca Park on June 28 for a lively 5K run or one mile walk and family friendly activities. Celebrate and support services for children with special needs while enjoying a community morning of..

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..