Trail Running calendar near Danbury 2026-2027

Looped 50-mile and 50k races in Prospect Park, Brooklyn on December 6, 2026, run on 3.33 mile laps starting and finishing near the Lincoln Road Entrance. Hydration is provided by Skratch Labs and a 15 hour cut-off applies.

A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

Trail races at South Mountain Reservation include 5K, 10K and 13.1 mile looped courses with aid stations every 3 miles. Courses use fire roads, single track, hills and some pavement and offer advance and day-of registration.

A winter trail party on a 5K loop offering 5K, 3 hour, 6 hour, and 3 hour rucking divisions, with proceeds benefiting the South Mountain Conservancy. The course mixes carriage roads and technical singletrack with about 300 feet gain per loo..

A onesie-themed 5K at Ramapo Valley County Reservation on February 14, 2027, run on a flat scenic loop around Scarlet Oak Pond. The event is capped at 200 participants, has no cutoff, offers adaptive support, and includes a finisher medal.

Trail races on a 10 mile loop at South Mountain Reservation offering 50M, 50K, 20M and 10M with marked trails, three aid stations per loop, timing, SWAG, and awards for top three male and female finishers.

Timed loop races on the Livingston Oval offer one, three, six and twelve hour options on a USATF certified flat course. Participants receive a hat and top finishers earn plaques.

A multi-loop trail race at South Mountain Reservation offering 11M, 20M, 50K and 50M options on three marked loops with varied terrain, significant elevation gain, a single finish-area aid station, and support for the South Mountain Conserv..

A chip timed 5K at Osprey's Dominion Vineyards in Peconic, NY on March 20, 2027. Entry includes a t-shirt, collapsible wine glass, finisher medal, chip timed bib and a pour of wine.

A 5K trail run at Bethpage State Park with a free kiddie fun run and a virtual option, a good luck shirt, on course hydration, post race refreshments, and age group recognition. Beer is available for participants 21 and older with ID.

On March 28, 2027 this roughly 16 mile out and back follows the Nipmuck Trail through Yale Myers Forest and Bigelow Hollow State Park. Registration opens Jan 1, 2027, parking is limited and a waitlist is used.

A 5K trail run and a free kiddie run at Bethpage State Park with in-person and virtual options, onsite refreshments, mailed bibs, and online results. Donations support the Never Stop Running Foundation.

A mountain trail event at Harriman State Park offering a half marathon, a 10K, and a 10K ruck on rugged, technical courses with significant elevation gain and limited crew access at aid stations.

Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT features a 25K loop with 3K+ of vertical and a 50K two-loop option. The course mixes technical singletrack and carriage roads, includes aid stations, and follows a cupless..

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY, on mixed terrain with dog friendly policies. Event proceeds support Last Chance Animal Rescue and online recognition is given for top age group finishers.

Trail races at Penwood State Park with a one loop 17K and a three loop 50K, about half on technical single track. The course is rocky and rolling, organized by the CT Trailmixers with proceeds to local land trusts.

A Spartan obstacle race weekend at Vernon Peak, NJ featuring Sprint to Ultra distances, a Kids Race, spectator access, and roughly 1,040 ft of vertical climb toward a 1,480 ft summit, with team options and a service member discount.

A women-centered trail event at Lake Mohegan offering 5K, 10K, and a 4-hour loop on a 3.2 mile trail. The race is open to non-binary runners, follows a cupless aid policy, and includes finisher medals and post-race refreshments.