Trail Running calendar near Woodbury 2025-2026

The Nipmuck South Trail Race is a scenic 15.7-mile out-and-back race held at Mansfield Hollow State Park in Connecticut. Participants will enjoy a beautiful course that follows the Fenton River, featuring varied terrain, small bridge crossings, and a climb to a 50-foot cliff. The event includes thre..

The Edge Hill Trail Race, scheduled for 2025, is a collaborative event with the Franklin Land Trust, celebrating the scenic trails and dirt roads of Ashfield. This race emphasizes a relaxed atmosphere, encouraging participants to enjoy the natural beauty while challenging themselves physically and s..

Manitou’s Revenge is a challenging 53-mile ultramarathon set in the scenic Catskill Mountains, starting in Windham, NY. The course features approximately 15,000 feet of elevation gain, with rocky and steep terrain that requires runners to be self-sufficient, as aid stations are limited. Participants..

The Summer Solstice Trail Run is an early morning summer event held in Gay City State Park, featuring three race distances: 3 miles, 5 miles, and 8 miles. The race is part of the Blue-Blazed Trail Running Series and the USATF-CT Mountain, Ultra, and Trail Series, offering a competitive team element..

The Free to Run Trail Races, organized by the Berkshire Ultra Running Community for Service (BURCS), will take place on June 21, 2025, in Pittsfield State Forest, Massachusetts. This event features three race distances: 15K, 25K, and 50K, designed to challenge participants with scenic trails and sig..

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 is an endurance race held in Roosevelt Forest, Stratford, Connecticut, featuring two main race options: a 33-hour challenge to run as many miles as possible or to complete 100 miles within 33 hours. The course is a 2.5-mile loop through classic New England terrain, in..

The Red Wing Trail Challenge is an annual trail running event held in Lagrangeville, NY, organized by Conquer The World Endurance. Participants can choose between a 60K race with approximately 6,600 feet of elevation gain or a 15K race with about 1,650 feet of gain. The course features a scenic 15K..

The 7-11 Slurpee Day Ultra 60k is a unique running event taking place in Vernon, CT, on July 11, 2025. Participants will cover a distance of 37.5 miles, primarily on roads, while making stops at various 7-11 locations along the route. This self-supported run encourages camaraderie and fun, with a so..

The Rails-to-Trails 5K in East Hampton is a point-to-point race starting at the Connecticut Draft Horse Rescue. Participants will be transported to the starting line via shuttle buses from Center School. The course features a scenic route along the Air Line Trail, concluding at the Old Home Days gro..

The Notchview Ultra is a multi-day ultramarathon event held from July 11-14, 2025, in Windsor, MA, at the scenic Notchview. Participants can choose from various race durations, including 6, 12, 24, 48, 72 hours, or a 100.7-mile race, starting at different times throughout the weekend. The course fea..

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 Soapstone Assault is a challenging approximately 5-mile trail race held at Soapstone Mountain, featuring a unique course that requires participants to climb the mountain six times. This event is designed for those seeking a rigorous hill workout, as runners navigate steep, rocky, and potentially..

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 trail run offers participants a scenic and challenging course through the beautiful People's Forest. The event is open..

The Sweltering Summer Ultra is an annual 8-hour running event held at Clapp Park in Pittsfield, Massachusetts. Participants can run or walk as many laps as they choose on a certified dirt and cinder track, with a total of 74 laps required for marathon completion. The event features a unique aid stat..

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..

The Stonington Cross Country 5K is a running event scheduled for August 13, 2025, in Pawcatuck, Connecticut. This event features a 5K race along with a Children's 1/2 Mile, catering to young participants aged 10 and under. The race begins on the track at Stonington High School, followed by a scenic..