Trail Running calendar near Shandaken 2025-2026

Join the Red, White and Run 5K trail run and walk at Veteran's Memorial Park in Lackawaxen on November 15, 2025. All paces welcome with day of registration and awards for top finishers across age groups.

Hit the trails at the Red, White and Run 5K in Lackawaxen's Veteran's Memorial Park on November 15, 2025. Enjoy a scenic trail run or walk, friendly competition, and awards for top finishers across age groups.

Run scenic, hilly single track at the Tarrywile Half Marathon on November 16, 2025 in Danbury CT with 10K, half marathon and marathon options. Rugged terrain, aid stations and finisher medals make for a rewarding trail day.

Brave frosty singletrack through scenic Ringwood woods with 5K, 10K and half marathon options for every trail runner. Finish with a warm post race party serving food, drinks and winter views.

Join the 4th Annual Sargent Elementary Turkey Trot in Beacon, NY for a family friendly 5K on the scenic Long Dock Park trails plus a Kids Fun Run on campus. Enjoy a food drive, live DJ, refreshments, awards and new team sign ups.

Join a scenic trail 5K or bring kids to a fun run at Hilltop Hanover Farm, a historic working farm and environmental center. This family fun fundraiser gives 5K finishers a $5 farm stand credit and supports the Friends of Hilltop.

Run a scenic trail half marathon around two glacial lakes and along the Shawangunk Ridge at Minnewaska State Park, with sweeping views into five states. Limited to 300 runners, chip timed with a finisher gift and refreshments.

Join the Roxbury Thanksgiving Charity Race, a scenic 5K in Roxbury, Connecticut, starting and finishing at Everett B. Hurlburt Community Park. Run or walk to celebrate the season and support local causes.

Join Somers' 7th Annual Thanksgiving Turkey Trot for a scenic but challenging 5K on the cross country trail and a family friendly 1 Mile fun run. Medals for all and shirts for early registrants add holiday cheer.

Take on a crisp late November trail at Stillwell Woods Preserve in Woodbury on November 30, 2025. Rob's Trail Run Edition features a scenic 5K with separate adult and high school youth divisions for runners of all levels.

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..

Enjoy winter trail runs and a snowshoe race at Chenango Valley State Park during the Binghamton Pond Festival, with festival vibes near the start. Choose 10k, 20k or 50k loops or a free kids run and support local youth programs.

Try snowshoe racing at Mountain Creek on January 31, 2026 with a scenic ridge 5k or a relaxed one mile finish. Ride the lift to the top, bring your own snowshoes, and enjoy a fun winter run for all abilities.

Celebrate Valentine's Day in a cozy onesie at the Squatchy Onesiefest 5K in Mahwah Feb 14. Enjoy a flat scenic trail loop around Scarlet Oak Pond with a fun run option, handcrafted finisher medal and a limited field for a festive race vibe.

Run rugged trails at Big Bear Squatch North in Harriman State Park on April 4, 2026 with half marathon, 10K and ruck divisions. Expect steep climbs, scrambling terrain and sweeping Hudson Valley and NYC skyline views.

Join the John Jay Community Trail Race in Cross River NY for a scenic hilly 5k, family friendly 4k walk and Kids Jay Dash on the track. Finish on the contest field, enjoy community built trails and snag a race shirt by registering early.

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.

Tackle rugged singletrack, cliffs and glacial ledges on the Shawangunk Ridge in this scenic mountain trail race offering 25K and 10 mile courses. Proceeds support Run Wild's campaign to protect Verkeerder Kill Falls.

Wawayanda Trail Fest in Hewitt New Jersey offers distances from a half marathon to a 100K through rhododendron tunnels, marsh bridges and winding single track. Aid stations and on site camping make for a friendly, challenging trail weekend.