Trail Running calendar near Danbury 2026-2027

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..

Take on rugged singletrack and carriage roads at the Frosty Fat Sass, a winter trail running and hiking event in West Orange's South Mountain Reservation. Choose a 5K loop or timed 3 hour and 6 hour options while supporting the South Mounta..

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 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.

Join the Squatchy Onesiefest 5K on Feb 14 in Mahwah NJ for a playful, flat 5K around Scarlet Oak Pond or a shorter fun run. Costume lovers earn awards for top finishers in onesies, with on trail aid and a cozy race village.

Run the Febapple Frozen in South Mountain Reservation, South Orange NJ, where four trail distances loop around a scenic 10 mile course in late February. Expect winter trails, aid stations, swag and timing for a hearty challenge.

Run or hike scenic woodland trails at Mahlon Dickerson Reservation in the Mahlon Winter Donut Run and Hike, with 5 or 10 mile options. All weather welcome and finishers receive a long sleeve shirt, medal and donuts.

Squatchapple is a scenic trail race at South Mountain Reservation in West Orange, NJ, with distances from 11 to 50 miles across three challenging loops. All finishers get a handcrafted wood medal and one shop item.

Enjoy a 34 mile point to point run along the scenic Lenape Trail, riding the train to the eastern start and finishing back at your car. Self supported with varied surfaces and skyline views, the route winds through parks, neighborhoods and..

Join the Never Stop Running Foundation 4 Leaf Clover 5K at Bethpage State Park, a scenic trail run starting on a grassy polo field. Family friendly with a kiddie fun run, virtual 5K and post race refreshments supporting the foundation.

The Ospreys Dominion Wine Run 5K will take place in North Fork on Saturday 21 March 2026. You can run 5 kilometers.

Tackle roughly 16 miles on the scenic, technical Nipmuck Trail in Union, Connecticut, running an out and back through Yale Myers Forest to Boston Hollow. Field capped at 100 with limited aid and no race day registration; proceeds support lo..

Run the 34 mile Lenape Trail from Branch Brook Park to South Mountain Reservation, passing parks and varied terrain, while supporting clean water projects. Solo runners get full crew support or join a 3 to 6 person relay.

Run Sleeping Giant State Park on scenic, challenging trails with 25K and 50K options. Tackle runnable miles, rocky singletrack and a steep scramble to sweeping views, while supporting the park through registration proceeds.

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.

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 a rugged, technical 10k through Van Cortlandt Park in the Bronx on March 29, 2026, and grab a commemorative souvenir. A portion of entry fees supports the Van Cortlandt Park Alliance for trail upkeep and youth programs.

Run rugged, technical trails at Bear Mountain with 10K or half marathon options and stunning Hudson Valley and NYC skyline views. Proceeds support the New York New Jersey Trail Conference; race day is Apr 4.

Join the Spring SOMO Timed Trail Races on April 4, 2026 in South Orange, NJ for looped trail fun at South Mountain Reservation. Pick a one or two loop race or challenge yourself in one, three, or six hour timed events on a 1.88 mile loop.

Run the Bunny Trail 5K at Bethpage State Park for a scenic start on the polo field and winding soft trails with a cross country feel. Family friendly with free kiddie run and virtual option, benefiting the Never Stop Running Foundation.