Trail Running calendar near Shandaken 2026-2027

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.

Hit the trails at the YETI OR NOT Snowshoe Invasion at Mountain Creek on January 31, 2026. Ride the lift to the top for a scenic 5k or untimed last mile welcoming runners, walkers and first time snowshoers. Bring your own snowshoes.

Join the Squatchy Onesiefest 5K on Feb 14 in Mahwah NJ for a playful, flat 5K around Scarlet Oak Pond or a shorter fun run. Costume lovers earn awards for top finishers in onesies, with on trail aid and a cozy race village.

A late-winter trail run at Gilbert Lake State Park offering 50K, 25K, and 10K on a marked 6-mile loop with aid at a lakeside cabin and proceeds supporting The Neighborhood Center.

Run rugged, technical trails at Bear Mountain with 10K or half marathon options and stunning Hudson Valley and NYC skyline views. Proceeds support the New York New Jersey Trail Conference; race day is Apr 4.

Run or walk the John Jay Community Trail Race in Cross River through scenic wooded trails and rolling hills, with 5k, 4k walk and a Kids Jay Dash on the track. A family friendly community event that finishes on the John Jay Contest Field.

Join the Brooklyn Cider House Spiked Apple 5K in New Paltz on April 19, 2026 for a chip timed run or walk. Enjoy a tee, cider pour, donut and a finisher medal that doubles as a bottle opener for a festive post race celebration.

Join the 10K Run for the Osprey at Lacawac Sanctuary on Sunday April 19 2026, with a scenic 10K trail run and a family friendly 5K walk supporting sanctuary conservation. Expect wooded trails, osprey sightings, and awards for top finishers.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 is a rugged trail test on the Shawangunk Ridge with a 25K and a 10 mile option over steep climbs and technical singletrack. Field capped at 150 and proceeds benefit Run Wild.

The Wawayanda Trail Fest will take place in Highland Lakes on Saturday 25 April 2026. You can run between 21 and 100 kilometers.

Celebrate the 52nd Jack Bristol Lake Waramaug Ultra on April 26 in Kent Connecticut with 100K, 50 Miler, and 50K options on scenic rolling loops around the lake. Fast paved roads, four aid stations, and a friendly finish at Lake Waramaug St..

Enjoy a spring 10k trail race in Cross River, NY on April 26, 2026, winding through scenic park trails. Entry is by lottery with registration opening January 2, 2026, perfect for trail runners seeking a well organized challenge.

Run to Remember on May 2, 2026 in Red Hook NY offers scenic 5K and 10K trail runs plus a 5K walk through meadows, orchards and forest. Honor loved ones and enjoy community spirit with cash prizes for top finishers.

Take on Breakneck Point Trail Runs in Beacon, NY on May 3, 2026, with half and full mountain courses over rugged, technical trails, steep climbs, and sweeping views. Expect big elevation, aid stations, informal camping, and a lively trail c..

Enjoy a scenic 5 mile trail run at Muscoot Farm in Katonah/Somers on May 17, 2026. Family friendly kids races and Farm Bucks to spend at the Muscoot Farmer's Market add festival fun after the finish.

C'mon Armageddon offers 50K, 10 Miler and 5 Miler trail races in Norvin Green State Park, featuring boulder fields, river crossings and steep climbs with skyline views. Awards and GAIA GPS routes make it a rugged, scenic challenge.

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.

Join the Mine Hill Half Marathon on May 24, 2026, starting and finishing at Mine Hill Distillery in Roxbury, CT. Tackle a scenic hilly road course and celebrate afterward with food, live music and distillery samples.

IronHike Spring 26 at Mohawk Mountain CT in June offers endurance routes from 15 to 152 miles for solo runners, teams and families in a flexible relay format. Enjoy basecamp camping, support stations and finisher gear.