Trail Running calendar near Stafford 2025-2026

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 buckles based on their completion time: Red for under 24 hours, White..

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 challenging 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 mix of gras..

The Notchview Ultra is an exciting multi-day running event scheduled for July 11-14, 2025, in Windsor, MA. Participants can choose from various race formats, including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours, all set on a scenic 1.9-mile loop trail. The event features well-s..

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

The Soapstone Assault is a challenging trail running event that takes place around Soapstone Mountain, covering approximately 5 miles. Participants will tackle a rigorous course that requires them to ascend the mountain six times, making it a demanding hill workout. The race features steep, rocky, a..

The Anchor Down Ultra is a prestigious ultra-marathon event held at Colt State Park in Bristol, Rhode Island. It features three race durations: 6-hour, 12-hour, and 24-hour, catering to various levels of endurance runners. Recognized as one of the "Best Races in America" by Men's Health Magazine, th..

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

The Stonington Cross Country 5K is a running event scheduled for August 13, 2025, in Pawcatuck, Connecticut. This race features a 5K course and a Children's 1/2 Mile, catering to participants of all ages. The race begins on the track at Stonington High School, followed by a scenic route that include..

The Jug End Loop Ultra is an exciting running event scheduled for August 23, 2025, at Jug End State Reservation in Egremont, MA. Participants can engage in a 6-hour ultra event, completing as many laps as possible on a scenic 4.2-mile course that features a mix of uphill and downhill terrain. The ev..

The TARC Fall Classic, hosted by the Trail Animals Running Club, takes place at Great Brook Farm State Park in Carlisle, Massachusetts. This popular running event features a variety of distances, including 10K, half marathon, 20 miles, 50K, and 50 miles, along with a free youth fun run. The scenic c..

The Macedonia Trail Race, held in Macedonia Brook State Park, Kent, CT, offers a unique trail running experience with stunning single-track paths, challenging climbs, and breathtaking viewpoints. Now in its 7th year, the event features three race distances: 50K, 25K, and 12K, catering to various ski..

The Wahaneeta Trail Run is a 5K trail race taking place in Westerly, Rhode Island, as part of the WTAC Fall Race Series. This event emphasizes a "no frills" approach, foregoing modern amenities like t-shirts and extensive awards to keep costs low and logistics simple. Participants can enjoy a classi..

The Pawling 24 Hour Trail Running Festival is an exciting endurance event taking place in Pawling, NY, featuring a variety of race options including 24-hour, 12-hour, 6-hour, and 3-hour challenges. Participants will run on a scenic loop course that combines pavement, grass, and single track trails,..

The Storybook Half Marathon is a friendly and inclusive running event taking place in Stratford, CT, on September 13, 2025. Participants can choose to run, jog, hike, or walk the scenic trail course, which features a mix of single and double track trails with some elevation. The event allows up to f..

The Wine Run at Westport Rivers Vineyard & Winery is a unique running event scheduled for September 14, 2025, in Westport, MA. Participants can enjoy a scenic 3-mile trail run through the vineyard, followed by an evening of dinner, wine, and live music. The event is designed for individuals aged 21..

The Charlie Stavros Memorial Beach Run is a free, end-of-summer 3-mile running event held at Westerly Town Beach, Rhode Island. Organized by the Westerly Track Club and the Stavros family, the race features a scenic route that includes a 1.5-mile out-and-back course along the beach at low tide. This..

The Cockaponsett Trails to a Cure is a trail running event taking place in Chester, Connecticut, featuring two race options: a 4-mile and a 9-mile course through the scenic Cockaponsett State Forest. The challenging terrain includes roots, rocks, and hills, with water stations provided along the rou..

The Angevine Farm Trail Festival, hosted by Steep Endurance, takes place in Warren, Connecticut, showcasing the region's scenic trails and beautiful fall foliage. This annual event features a variety of races, including a Half Marathon, 5K, and a unique 8-hour challenge, all set against a backdrop o..

The IronHike Endurance Series, taking place at Mohawk Mountain in Cornwall, CT, is a unique multi-day event designed for both individual participants and teams. Scheduled for October 2-5, 2025, it features various challenges, including the Kuwohi, Double K, Denali, Everest, and Olympus Mons Ultra, e..

The Run for the Pumpkins Trail Run, organized by the Westerly Track & Athletic Club, is part of the WTAC Fall Race Series and will take place at Bradford Preserve in Westerly, Rhode Island. This event features a 10K, 5K, and a children's 1K run for participants aged 10 and under. The courses showcas..