Trail Running calendar near Shandaken 2025-2026

Get festive at the Ugly Sweater 5K in Canajoharie on December 6, 2025, where runners and walkers hit the scenic Erie Canal trail in holiday style. All proceeds support the Community Youth Center and age group prizes add extra fun for racers..

Join Pond Fest Winter Trail Runs and Snowshoe at Chenango Valley State Park during the Pond Festival for scenic looped trails from 10k to 50k and a kids race. Crowds and aid at the start and finish make for a lively, supportive day.

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.

Run the Squatchy Onesiefest 5K on Feb 14, 2026 in Mahwah NJ, a flat, scenic trail loop around Scarlet Oak Pond with a shorter fun run option. Wear a onesie for award eligibility and help support NYNJTC trail maintenance.

Try the Fire and Ice Winter Run at Gilbert Lake State Park for scenic snowy loops on forest, gravel and road with options for 10K, 25K or 50K and snowshoes welcome. Warm aid, coffee and fireplaces at the Briggs cabin and proceeds support a..

Tackle technical, rugged trails and steep climbs at Big Bear Squatch North in Bear Mountain NY on April 4, 2026. Choose a challenging 10K or a grueling half marathon, with proceeds supporting the New York New Jersey Trail Conference.

Join the John Jay Community Trail Race in Cross River NY on Sunday April 12, 2026 for a family friendly outing with a 5k, 4k Jay Walk and a 200 meter Kids Dash. Race on scenic wooded, hilly school trails and finish at the track.

Celebrate spring at the Brooklyn Cider House Spiked Apple 5K on April 19 in New Paltz, a scenic two lap run through vineyards and orchards. Enjoy a cider pour, fresh donut, finisher medal and commemorative shirt.

Join a scenic 10K trail run or a relaxed 5K walk at Lacawac Sanctuary in Lake Ariel on Sunday April 19 2026. Enjoy woodland trails and osprey views by Heron Pond while supporting upkeep of Browning Beaver Meadow.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 serves up technical singletrack on the Shawangunk Ridge with 25K and 10 mile options, big climbs and sweeping Catskill views. This rugged trail event also supports protection of..

Explore rugged single track, rhododendron tunnels and marsh bridges at Wawayanda Trail Fest in Hewitt, NJ. Choose distances from half marathon to 100K on a scenic 26 mile loop with supportive aid stations and on site camping.

XTERRA New Jersey at Wawayanda State Park is a weekend off road race festival with trail runs, mountain and gravel biking, triathlons and a paddle triathlon. Camp lakeside and soak up live beach music between races.

Run the 52nd Jack Bristol Lake Waramaug Ultra Races on April 26, 2026 in Kent CT with 100K, 50 mile and 50K options around scenic Lake Waramaug. Flat rolling loops, four aid stations and finisher swag make this a rewarding spring ultra.

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.

Join A Run to Remember on May 2 in Red Hook and run or walk scenic farm trails through meadows, orchards, and woods at Greig Farm. Honor loved ones, celebrate community spirit, and vie for cash prizes in the 5K and 10K races.

Take on Breakneck Point on May 3, 2026 in Beacon, NY with a rugged half or full ultramarathon featuring huge elevation and technical single track. Expect steep exposed climbs, aid stations, and a finisher shirt and memento.

Run scenic trails at Muscoot Farm in Katonah on May 17 with a 5 mile race and kids events for ages 2 to 12. Finishers get Farm Bucks for the farmers market and proceeds benefit local charities; order shirts early.

C'mon Armageddon is a rugged trail race in Norvin Green State Park NJ offering 50K, 10M and 5M routes over boulder fields, river crossings and rocky peaks with skyline views. Big climbs and technical terrain make it a true test.

Run Like The Wind 5K in Ellenville offers a scenic course along the Shawangunk Mountains and the newly resurfaced Rail Trail. Finish at Aroma Thyme Bistro for garden drinks and food while supporting local food pantries and youth scholarship..

Recharge your trail legs with a small group spring camp in Oliverea, NY, in the Catskills. Tackle technical scrambles and big climbs while getting on trail coaching and mental performance work to sharpen your skills and confidence.