Trail Running calendar near Cheshire 2025-2026

Join a friendly, informal 5 to 10k run or snowshoe on a roughly 10k course with loaner snowshoes available. Bring a spare pair to share, enjoy light refreshments, and team up for bragging rights and a shared baked treat.

Join the Frozen Heart 900, a free grassroots winter loop in Rockfall CT where runners take on a 15 hour challenge around a 2.2 mile trail loop. Self supported format with a heated meeting room for warming, so bring headlamps and carpool.

Squatchy Onesiefest 5K at Ramapo Valley is a festive trail run with a handcrafted finisher medal and awards for onesie wearers. Limited to 200, the flat gravel loop welcomes road shoes and offers aid and parking.

Run the 4 Leaf Clover 5K at Bethpage State Park on March 8, 2026. Enjoy scenic soft trails, a free kiddie Clover run and a one week virtual 5K, plus a themed shirt while supporting the Never Stop Running Foundation.

Run or walk a chip timed 5k through scenic vineyard trails at Osprey’s Dominion Vineyards in Peconic, NY. Finish with a finisher medal that doubles as a wine stopper, a keepsake wine glass and a post race pour for eligible participants.

Test your trail skills on the Northern Nipmuck Trail Race, a rugged 16 mile out and back through Yale Myers Forest and Boston Hollow with technical terrain and serious climbing. Limited to 100 entrants, proceeds support local trails.

Tackle rugged singletrack and steep rock scrambles at the Sleeping Giant Trail Runs in Hamden CT on March 29, 2026. Choose a challenging 25K loop or a double 50K and enjoy aid stations, medals and post race food and drinks.

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 CT123 on April 4, 2026, a point to point 123 mile ultramarathon across Connecticut that blends trails and backroads for a challenging spring adventure. Solo and relay entries welcome and 200K finishers earn a commemorative belt buckle.

Join the Bunny Trail 5K at Bethpage State Park for a family friendly run starting on a grassy polo field and winding onto scenic soft trails. In person and virtual entries plus a free kiddie run support the Never Stop Running Foundation.

Run a scenic quarter marathon at West Hartford Reservoir on April 11, 2026, as the Hartford Track Club hosts a small, timed field limited to 150 runners. Enjoy chip timing, post race treats and a friendly, looped trail course.

Join Run for the Rescue on April 11, 2026 for a scenic 5K through Blydenburgh County Park with on site and virtual options. Tackle varied trails, enjoy post race refreshments, and support Last Chance Animal Rescue.

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.

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.

Run the scenic Shore2Shore trail event from Sunken Meadow to Heckscher State Park on Apr 18, 2026, with 25K and 50K options along the Long Island Greenbelt Trail. Well stocked aid stations, shuttle service and a logo shirt make for a memora..

Take on rugged Traprock at Penwood State Park in Bloomfield CT on April 18, 2026 with 17K one loop or 50K three loop options. Expect rolling, technical single track and rocky trails; bring your own cup for this cupless, chip timed race.

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.

Run the Brooklyn Cider House Spiked Apple 5k in New Paltz on April 19, 2026 for a chip timed 5K through cider country. Enjoy a homemade cider donut, a pour of cider and a finisher medal that doubles as a bottle opener.

Squatchywaska Mountainfest in Ellenville offers adventurous 25K and 10 Mile trail runs on the Shawangunk Ridge with steep climbs, technical singletrack, and stunning views. Entry is capped at 150 and proceeds help protect Verkeerder Kill Fa..

Join the Lake Mohegan Women’s Trail Race at Lake Mohegan in Fairfield CT for 5K, 10K or a 4 hour loop challenge open to women and non binary runners. Enjoy scenic trails, finisher medals, post race snacks and a welcoming community vibe.