Trail Running calendar near Red Hook 2025-2026

Take on the Tower Tag Challenge at Sleeping Giant State Park on December 6 with 4 hour or 8 hour timed options of repeated out and back laps to the park observation tower. Enjoy the scenic climb, earn a finisher medal, and support the park.

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..

Run the Frosty Forest 5K in Stratford through Roosevelt Forest on an off road trail welcoming runners, joggers and walkers. Holiday costumes encouraged, every finisher gets a commemorative item and proceeds support local charities.

Join the 8th Annual Taco Trials in Rocky Hill: eat a taco then run a 1 mile loop, repeating it ten times for a fun, quirky challenge. Medals for finishers and proceeds benefit the Connecticut Forest and Park Association.

Seth's Fat Ass 50K at Forest Park in Springfield is a friendly challenge of up to ten 5K loops. You have seven hours to run as many laps as you like, grab event schwag and a t shirt, and enjoy the social ultrarunning vibe.

The Dar Snowshoe Scramble will take place in Goshen on Sunday 25 January 2026. You can run 10 kilometers.

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.

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 the Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT on March 29, 2026 with 25K and 50K options across rugged singletrack and big climbs. Expect steep scrambles, more than 3,000 feet of gain per loop, cupless aid s..

Take on the Fools Adventure, a 10 hour rogaine across roughly 8 square miles of North Jersey wilderness near Wayne, NJ on March 29, 2026. Solo navigation with map and compass and visits to over 100 checkpoints will test your route choice an..

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.

Run a scenic 6.55 mile quarter marathon through West Hartford Reservoir 4 as two loops around the park. Limited to 150 runners, the event features chip timing, post race treats and awards in five year age groups.

Join the John Jay Community Trail Race on Sunday April 12 2026 in Cross River NY for a scenic 5k on wooded trails, a 4k community walk and a 200 meter kids dash on the track. Early preregistered participants get race shirts.

Tackle wooded trails at the Farm & Forest All Terrain 5K and Hog Wild Kids Fun Run in Stamford, CT on April 12, 2026. Family friendly and community focused, this race raises funds for the Stamford Museum and Nature Center.

Tackle rugged trails at Penwood State Park in Bloomfield CT with the Traprock race, offering a single loop 17K or a three loop 50K on scenic, rocky Metacomet Trail. Hosted by CT Trailmixers, this cupless trail run supports local land trusts..

Join the final Conquer The Trail Race on April 18 in Dobbs Ferry for a scenic 7.5 km on the Croton Aqueduct Trail supporting Mercy University's Mav Market. Mostly flat trail with natural obstacles, raffles and shirts for early registrants.

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.

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.