Trail Running calendar near Woodbury 2026-2027

Run the historic 34-mile Lenape Trail from Newark to Millburn, traversing 18 parks. Choose to go solo or as a relay team, with full support including aid stations and shuttles. This charity event supports MissionCleanWater's work to provide..

A roughly 5-mile single-track trail race at Chimney Rock Park on March 28, 2026, featuring rocky single track, stream crossings, course marshals, a water stop passed twice, age-group awards, and a post-race pizza party.

Experience a technical trail race at Chimney Rock Park featuring rocks, roots, and stream crossings. This established five mile event concludes with a community pizza party and awards for various age categories.

Experience a variety of technical trails and rock scrambles in Connecticut at the Sleeping Giant Trail Runs. Choose between 25 km and 50 km distances featuring significant elevation gain and historical park landmarks.

A 5K and 10K trail run at Central Park of Morris County on March 29, 2026. The mixed terrain course includes dirt, grass, gravel and hills, and registration includes a shirt, finisher medal and empanada.

Mudders and Grunters is a trail race in Yorktown Heights on March 29, 2026, featuring an approximately 5 mile single loop through mud, water crossings and some hills. It is part of the 2026 Trail Mix Series.

A trail event in Van Cortlandt Park on March 29, 2026 featuring a hilly 10K and a 0.5 mile kids run. Partial proceeds support the Van Cortlandt Park Alliance and prizes include carrot cake and muffins.

Run the perimeter of Heckscher State Park on smooth trails. Choose a 7-mile or 14-mile loop for a cupless, manually timed race. All finishers get a wooden medallion and a bucket hat.

Experience a scenic trail run through Bethpage State Park with the 4 Leaf Clover 5K. Enjoy a mostly flat course, post race refreshments, and a festive atmosphere supporting the Never Stop Running Foundation.

Experience a technical mountain trail race at Harriman State Park featuring steep climbs and rock scrambling. Choose between 10K and Half Marathon distances with stunning views of the Hudson Valley and NYC skyline.

Experience a clockwise loop race at South Mountain Reservation featuring timed options from one to six hours. This event offers a 1.88 mile course consisting of single track paths and fire roads for all distance preferences.

Experience the single track and gravel trails of Jacobsburg State Park in this zero carbon event. Choose between a fixed five mile loop or timed sessions of three and six hours.

Experience the 7th Annual Bunny Trail 5K at Bethpage State Park. Run or walk through scenic soft trails and grassy polo fields with options for an in person race, a virtual challenge, and a free kids run.

Experience an authentic off road adventure in Guilford with a 10k trail loop featuring technical single track paths and rock scrambles through Westwoods to support local land conservation.

Run a unique quarter marathon distance on the paved trails of West Hartford Reservoir. This chip timed 6.55 mile race features a two loop course with post race treats and age group awards.

Join this dog friendly 5K trail run at Blydenburgh County Park to support animal rescue. Enjoy a scenic multi surface course with refreshments and professional timing included for all participants.

Run or walk the scenic trails at Institute Woods. This 6K event offers a shorter 3K option for walkers and is limited to 200 participants. Post run refreshments await all finishers.

Experience a community trail event in Cross River featuring a competitive 5k race, a scenic 4k walk, and a 200m kids dash. Explore the wooded hills of the John Jay Community Trail ending at the campus contest field.

Experience a unique all terrain run through Heckscher Farm and wooded trails in Stamford. Runners pass farm animals and historic landmarks on a scenic course while children enjoy a dedicated fun run and educational activities.

Experience a beautiful trail run through the Irvington Woods with 5K and 1K distances. This rain or shine community event features finishers medals for all participants and supports the Irvington Bulldog Booster Club.