Trail Running calendar near Fairfield 2025-2026

Join the 8th Annual Taco Trials in Rocky Hill CT: eat a taco then run a one mile loop, repeat ten times for fun and trophies. All proceeds benefit the Connecticut Forest and Park Association and the event is full with a waitlist.

Seth’s Fat Ass 50K at Forest Park in Springfield on December 20 invites runners to tackle between one 5K loop and the full ten loop 50K in a festive, low key winter setting. Enjoy scenic roads and trails, event swag and a seven hour limit.

Run the Last Supper 100k in Roxbury NJ on Dec 27, starting at Horseshoe Lake. Choose solo or relay teams up to 10 and tackle scenic trails and lakeside roads for a winter ultramarathon adventure.

Hit the trails at South Mountain Reservation on January 10, 2026 for NJ Trail Series SOMO Winter 3, with 5K, 10K and 13.1 mile looped courses over hills and single track. Aid stations, on site registration and a giveaway add winter race day..

Join the ninth annual Frosty Fat Sass at South Mountain Reservation, a fundraiser for the South Mountain Conservancy. Choose a 5K, timed 3 or 6 hour loop or rucking division on a rugged, rocky 5K trail.

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 Morris County Empanada Trail on March 29 in Morris Plains NJ with 5K and 10K runs over scenic mixed terrain. Entry includes a long sleeve shirt, finisher medal and an empanada with proceeds benefiting the Arthritis Foundation.

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.

Join Febapple Frozen on Feb 21, 2026 in South Orange / Maplewood, NJ for a winter trail challenge on a 10 mile loop through South Mountain Reservation, with distances from 10 miles to 50 miles. Aid stations, official timing and event swag m..

Run or hike rugged woodland trails at the Mahlon Winter Donut Trail Run and Hike, with 5 and 10 mile options around Saffin's Pond. Trail markers keep you on course and the event runs rain, snow, or shine for a true winter adventure.

Squatchapple puts scenic singletrack and carriage road loops in South Mountain Reservation to the test with distances from 11 miles to 50 miles. Support the South Mountain Conservancy and earn a handcrafted wood medal and race swag.

Tackle a scenic 34 mile out and back along New Jersey's Lenape Trail, from South Mountain Reservation through Newark and back, with skyline views and varied terrain. This self supported adventure asks runners to carry their own gear and nut..

Run the Never Stop Running Foundation 4 Leaf Clover 5K at Bethpage State Park on March 8 2026 for a scenic trail 5K across grassy polo fields and winding soft trails. Family friendly with a kids run, virtual race and refreshments.

Enjoy a scenic 5K around Osprey's Dominion Vineyards in Peconic, NY on a two lap cross country style course for runners and walkers. Finishers get a shirt, bottle stopper medal, shatterproof wine glass and a wine pour.

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.

Explore rugged North Jersey wilderness in The Fools Adventure, a 10 hour foot ROGAINE with over 100 checkpoints across scenic, rocky terrain. Test your map and compass skills as you navigate for the best route and enjoy big views.

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 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.

Spring SOMO Timed Trail Races in South Orange this April on a 1.88 mile loop offer one loop or 1, 3 and 6 hour timed options. Expect single track, pavement and fire road through scenic South Mountain Reservation.

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.