Trail Running calendar near Naples 2026-2027

Experience a winter trail challenge on January 31, 2026 at Mendon Ponds Park, with a scenic loop around Devil's Bathtub and warm aid station comforts at Hopkins Point Lodge. Choose from 50k, 25k or 5 mile options as part of the Common Groun..

Beast of Burden Winter is a chilly ultramarathon in Lockport, NY with 25, 50 and 100 mile options on February 7, 2026. Run the scenic Erie Canal towpath where snow is possible and enjoy warming shelters and hot aid station fare.

Cabin Fever Trail Races in Webster Park on February 22, 2026 feature approximately 5 and 10 mile winter trail courses through pine woods, a long sleeve shirt for early registrants, post-race food, and age-group awards.

Run Maple Madness: Mud, Sweat, & Syrup in a 5K or 10K on scenic farm trails with maple syrup shots on course. Celebrate at the finish with pancakes, sap house tours and a cozy bonfire plus a souvenir bottle of syrup.

Run or walk a chip timed 5K through scenic vineyards and orchards at Three Brothers Wineries and Estates. Enjoy a cider donut, shirt and a finisher medal that doubles as a bottle opener, with family friendly and virtual options.

Run a scenic 5K through trails and vineyards at Spring Lake Winery in Lockport on April 4, 2026. Enjoy finish line snacks, a keepsake wine glass, and post race food and drinks with live music and festivities.

English's Ridge Rumble at Green Lakes State Park in Fayetteville NY offers 50 km, 20 mile and 10 mile trail distances. Run varied trails around the park's striking blue green meromictic lakes for a scenic and challenging mid April outing.

Muddy Sneaker 20K invites runners to tackle rugged Finger Lakes trails near Canandaigua Lake. Expect steep climbs, natural obstacles and playful chaos in a gritty, scenic 20K with limited entries.

DENFIT ULTRA at Buffalo Ski Center is a 10 km ski slope loop with 50k or 100k options, offering big elevation and possible snow. Parts are unlit so headlamps are required and finishers earn medals and custom spears.

Take on a scenic single track loop around Hills Creek Lake in Wellsboro, PA and run as many 3 mile loops as you can in 3, 6 or 12 hours, or field a 12 hour relay team. Camping is available nearby and the event runs rain or shine.

Hit the trails at Medved Madness in Mendon Ponds Park with long, short and kids course options. Long and short finishers receive gender specific technical shirts and everyone can unwind at an after race barbecue.

Forest loop event at Greek Peak near Cortland, NY on May 9, 2026 offering 7, 14, 21 and 28 mile options. Walk or carry 10, 20 or 35 lb and finish within 10 hours to earn patches and medals.

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.

Take on the Susquehannock Trail Ultra in Coudersport PA on May 16, 2026, an 83 mile single track challenge with over 14,000 ft of climbing. Rugged navigation and remote aid stations make this a true endurance test with a 36 hour cutoff.

Join Sand to Serengeti at Green Lakes State Park on May 17, 2026 for scenic 10 mile and 3 mile runs from the beach around Round Lake to the Serengeti ridge. Supports Safe Space Organization. Finishers get a medal or towel.

Run through Letchworth State Park at the Vale of Three Falls on May 17, 2026, choosing from 5K, 10K, or 15K distances. Expect rolling hills, scenic Genesee River overlooks on stone and gravel roads, and a festive finish at the Parade Ground..

UltraTrax Holiday Valley is a timed outdoor trek across wooded single track trails and ridgelines at Holiday Valley, with options from 7 to 28 miles and a 10 hour cutoff. Enjoy a marked course, finishers gear and a post trek party with food..

Run through the gorges and waterfalls of Robert H. Treman State Park from the Old Y Camp, tackling mostly singletrack and historic stone stairs. Choose 50 mile or 50K options and enjoy finisher swag, hearty aid and scenic New York trails.

Lucifer's Crossing at Robert Treman State Park offers half marathon, 10K and 5K trail races through the scenic Lucifer Falls gorge. Expect rolling climbs, historic stone steps and mostly singletrack for a rewarding trail challenge.

Hit the trails at Frost Town Trail Fest on June 6 in Naples, NY, for scenic single loop routes around the Cumming Nature Center with challenging climbs and a kids fun run. Multiple distances, a friendly race vibe, and beautiful lake and for..