Trail Running Calendar New York 2026-2027

Run or walk the Ledge Rock Hill Wine Run 5k at Ledge Rock Hill Winery in Lake George on Sunday May 17 2026, a scenic vineyard course welcoming all paces. Enjoy a T shirt, collapsible wine glass and finisher medal while supporting Nik's Wish..

Run Like The Wind 5K in Ellenville winds along the base of the Shawangunks and a scenic stretch on the Rail Trail. Finish in Aroma Thyme Bistro's garden with beer, wine and food while supporting food pantries and youth scholarships.

Sharpen your trail skills at a three day Spring Training Camp in Oliverea NY. Expert coaching and guided runs on technical Catskill ridgelines include a 13 mile day with 5000 ft of climbing, plus lodging, meals and great camaraderie.

Run or walk the Never Stop Running Foundation Long Island Lemonade Trail 5K on May 23, 2026 at Blydenburgh County Park, with an in person or virtual option. Free Kiddie Dash and proceeds benefit the foundation.

Join the Forest Park Runners Classic, a scenic 4 mile road and trail out and back in Forest Park, Queens, on Sunday May 24, 2026, featuring chip timing and an overhead finish clock. Pre register for a tech shirt and enjoy post race snacks a..

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..

Take on ski slopes and mountain trails at Plattekill Mountain Race in Roxbury NY on June 7, 2026. Choose the tough 6.5 mile mountain course with massive elevation gain or the steep, punchy 5k that climbs hard out of the gate.

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.

Manitou’s Revenge in Windham, NY on June 20, 2026 is a 53 mile ultramarathon across the Catskills with about 15,000 feet of climbing and rugged, technical trails. Expect long self supported stretches and routes that get harsher after dark.

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.

Run a scenic chip timed 5K through Sheldrake Point Winery vineyards overlooking Cayuga Lake on wide grass and packed dirt trails. Enjoy live music, food trucks and a complimentary glass of wine for those 21 and over.

Celebrate July 4th at Whiteface Mountain Resort in Wilmington NY with a summit finish atop alpine slopes and serious elevation gain. Race a 10k, a two loop SkyRace, or the Vertical K, then join informal Sunday group runs.

Celebrate July 4 with Finger Lakes 50s, a looped trail race in Finger Lakes National Forest near Hector NY offering 50 miles, 50K and 25K options on mostly single track with rolling climbs. Camp in the forest and enjoy awards and a BBQ at t..

Run the Red Wing Trail Challenge in Lagrangeville, NY on July 5 with 15K, 30K, and 60K options on a runnable 15K loop with varied terrain and serious climbing. Aid stations, lap base for 60K, and post race food make this a true trail day.

Pinky's Rock n Rolla is a lively 4 mile trail race through Forest Park's scenic trails celebrating Pinky the Pacer. Finishers get medals, top three men and women earn prizes, dogs welcome, and proceeds benefit Puppy Kitty NYCity.

Experience rugged Finger Lakes scenery at the High Tor Trail Marathon in Naples, NY on July 11, 2026, starting and finishing at Naples Community Park. Expect challenging climbs, flowing downhills and two scenic loops for the full marathon.