Trail Running calendar near Penn Yan 2026-2027

We have found 39 Trailruns within 80 miles of Penn Yan. See below where and when you can find the races.

Tackle snowy trails in Ontario County Park at Mrs. McCormick's Ice House, a winter trail race offering 4, 8 or 12 mile options on a scenic loop. Finish with pancakes, hot drinks and a cozy lodge atmosphere to warm up and celebrate.

Join Pond Fest Winter Trail Runs and Snowshoe Race at Chenango Valley State Park for scenic 10k loops you can repeat to suit any distance, including a kids run. Enjoy festival vibes with food trucks, ice events, and community spirit.

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..

February 2026

Shake off winter with the Cabin Fever Trail Races at Webster Park, offering 5 and 10 mile trail loops through scenic, rolling terrain. Expect variable winter trail conditions, warm post race food, and a friendly community vibe.

March 2026

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.

April 2026

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.

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.

UTMB Index

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.

May 2026

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.

Enjoy spring single track and ridge views at UltraTrax Greek Peak, a timed walking event with 7 to 28 mile loop options at Greek Peak Mountain Resort. Challenge yourself with a weighted vest and support the Conservation Lands Foundation.

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..

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.

June 2026

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..

YMCA Race Weekend at Green Lakes State Park features two days of triathlon, duathlon, aquabike, aqua run and an 8K trail through scenic lakes and old growth forest. Family friendly fun and a kids run raise funds for YMCA programs.

Many On The Genny is a scenic all trail challenge at Letchworth State Park with a 45 Miler and relay options along the park gorge. Expect single track, vistas, climbs and remote aid sections that reward prepared runners.