Trail Running calendar near Woodbury 2025-2026

The NSRF Long Island Lemonade Trail 5K is a vibrant running event taking place at Blydenburgh County Park on May 24, 2025. This trail run offers participants a refreshing experience as they navigate a mix of pavement, dirt roads, and hard-packed trails. The event includes a free Kiddie Dash and feat..

The Mine Hill Half Marathon, organized by Steep Endurance, is touted as one of the toughest road half marathons in Connecticut. Set against the stunning backdrop of the Mine Hill Distillery in Roxbury, participants will enjoy breathtaking views of farms and fields while navigating a challenging cour..

The Forest Park Runners Classic 4 Mile Road and Trail Race is set to take place on May 25, 2025, at Victory Field Track in Woodhaven, NY. This event features a scenic 4-mile out-and-back course through the beautiful trails and roads of Forest Park. Participants can expect custom technical T-shirts a..

The Peach Hill "Run For the Hill of It" 5K is a cross-country running and walking event taking place at Peach Hill Park in Poughkeepsie, NY. Participants will traverse scenic trails, reaching the highest point in the town for stunning views. Open to all ages, the event encourages both runners and wa..

The IronHike Endurance Series - Spring 2025 takes place at Mohawk Mountain in Cornwall, CT, from June 5 to June 8, 2025. This unique event combines hiking and trail running, offering participants various challenges, including individual and team formats. Events range from 12 to 84 hours, with distan..

The Sri Chinmoy 24-Hour, 12-Hour, and Midnight Marathon is a running event taking place at Rockland Lake State Park, NY, on June 7-8, 2025. Participants can choose from three race formats: a 24-hour race, a 12-hour race, or a midnight marathon. The course features a scenic, flat, and fast 2.95-mile..

The XTERRA Transcend Trail Run, taking place on June 14, 2025, in Randolph, New Jersey, is an exciting outdoor event featuring a variety of trail races, including a Half Marathon, 10K, and 5K. Set in the picturesque Dickerson Mine Preserve, participants will enjoy fast, flowing singletrack trails wi..

The Ansonia Six Hour Trail Run is an exciting endurance event taking place at the Ansonia Nature Center in Ansonia, Connecticut. Participants will tackle approximately 1.9-mile loops on moderately technical singletrack trails, featuring about 170 feet of elevation gain per loop. Scheduled for the se..

TPK Bad Decisions is an exciting 30-hour team event held in Andover, NJ, where four-person teams tackle a series of mandatory challenges. This unique competition combines elements of adventure racing and problem-solving, requiring participants to navigate, carry heavy loads, and complete various tas..

The Brooksvale 12-Hour event is a unique running challenge taking place in Hamden, CT, where participants can test their endurance over a 12-hour period on a scenic 4.25-mile loop with a total elevation gain of 500 feet. Runners can aim for various distances, including 50 miles, marathons, or 50k, m..

The Centurion Ultra Trail Event, part of the Roosevelt Forest Ultras series, is set to take place in Stratford, Connecticut, featuring a challenging 100-mile race with a loop course of 2.5 miles. Participants can earn one of three unique buckles based on their completion times: Red for under 24 hour..

The Red Wing Trail Challenge, organized by Conquer The World Endurance, is set for July 6, 2025, in Lagrangeville, NY. Participants can choose between a 60K race featuring approximately 6,600 feet of elevation gain and a 15K race with about 1,650 feet of gain. The event promises a scenic trail exper..

The Rails to Trails 5K is a scenic point-to-point race held in East Hampton, CT, as part of the Old Home Days celebration. The race begins at the Connecticut Draft Horse Rescue and features a route that includes a shaded stretch along the Air Line Trail. Participants can enjoy a water station along..

Pinky’s Rock n Rolla is a unique trail running event taking place in Richmond Hill, NY. This four-mile race offers participants the chance to experience actual trail running through the scenic Forest Park, featuring natural terrain shaped by glaciation. The event is designed for both newcomers and s..

The Squatchy Surprise is an exciting endurance event taking place at South Mountain Reservation in West Orange, New Jersey, on July 26, 2025. This unique trail running experience challenges participants to draw colored golf balls to determine which of four loops they will run, adding an element of c..

The Second Annual Orange Runners Club Summer Sizzle XC5k is set to take place at the Rich Furst Sanfordville Elementary School XC Course in Warwick, NY. This exciting event features a 5k run or walk, along with a Kids Dash, promoting teamwork, dedication, and fun in the spirit of cross country runni..

The MCW Westfield Ultra is an annual running event hosted by MissionCleanWater at Tamaques Park in Westfield, NJ. Participants can choose to run for 3, 6, 9, 12, or 24 hours, completing as many laps as possible around a 0.8-mile loop. The event welcomes runners of all skill levels and includes a fun..

The People's Forest 7-Mile Trail Run, now in its 26th year, is a prominent event in the USATF/CT Mountain Ultra Trail series. Scheduled for August 2, 2025, in Barkhamsted, CT, this race offers participants a scenic and challenging trail experience. The event is dedicated to the memory of Peter Hawle..

The Running Wild at Wildwood 2.5 Mile Trail Run is an exciting outdoor event taking place at Wildwood State Park in Wading River. Scheduled for August 9, 2025, this trail run invites participants of all skill levels to enjoy the scenic beauty of the park while engaging in a healthy and fun activity...

The Interstate 17 Trail Run, taking place in Closter, NJ, is a challenging 17-mile race designed for experienced runners. Participants will navigate a rugged course featuring over 5,000 feet of elevation change, with stunning views along the Hudson River. The race consists of four loops, including a..