Trail Running calendar near Great Barrington 2025-2026

The Camp Saratoga 8K Snowshoe Race is an annual event held at the Wilton Wildlife Preserve & Park in Gansevoort, NY. Scheduled for February 8, 2025, this race invites participants to enjoy a scenic snowshoeing experience. Registration is available on the day of the event, with a fee increase for sam..

The Spring On The Trails Endurance Runs is an exciting annual event held in Lagrangeville, NY, featuring timed races of 3, 6, and 12 hours on a scenic 5k trail loop with approximately 250 feet of elevation gain per lap. Participants aim to complete as many loops as possible within their chosen time..

The Northern Nipmuck Trail Race is a 16-mile trail running event held in Union, Connecticut, organized by the Shenipsit Striders. Revived in 2022 after a hiatus, the race maintains a friendly, low-key atmosphere, attracting runners of all levels. The course traverses the Nipmuck Trail, featuring tec..

The Enchanted Forest Ultra Run is a unique 6-hour trail race set to take place on March 29, 2025, in Stratford, CT. This event features a 2.3-mile loop course with an elevation gain of 191 feet, perfect for both novice and experienced runners. Participants can run, jog, hike, or walk as many laps as..

The Sleeping Giant Trail Runs is a challenging new race set in one of Connecticut's iconic parks, known for its diverse trails. Participants can choose between a 25K and a 50K course, both featuring over 3,000 feet of elevation gain. The event showcases a mix of smooth carriage roads and technical,..

The Big Bear Squatch North is a challenging trail running event taking place at Harriman State Park in Bear Mountain, New York. Scheduled for April 5, 2025, this event features a half marathon and a 10K race, both known for their rugged terrain, steep climbs, and breathtaking views. Participants can..

The Mt. Toby Ultra is a trail running event offering three distance options: 13k, 24k, and 50k, each showcasing the scenic beauty of Mt. Toby.The race serves as a fundraiser for Girls on the Run of Western Massachusetts, promoting joy, health, and confidence among girls through running. Participants..

The Farm & Forest All-Terrain 5K & Kid Fun Run is scheduled for April 6, 2025, at the Stamford Museum & Nature Center in Stamford, CT. This exciting event features a scenic 5K course that begins at the Fedele Family Plaza and winds through Heckscher Farm, allowing participants to encounter various f..

The John Jay Community Trail Race is a competitive running event taking place in Cross River, NY, featuring a 5k race, a 4k Jay Walk, and a Kids Jay Dash. The 5k course winds through the scenic John Jay Community Cross Country Trail, offering challenging and hilly terrain. The 4k Jay Walk is a non-c..

The Traprock 50 is a challenging trail running event held at Penwood State Park in Bloomfield, CT, featuring two race distances: a 50K and a 17K. The course consists of approximately 10.5-11 miles per loop, with the 50K requiring three loops and the 17K one loop. Runners will navigate a mix of techn..

The Lake Mohegan Trail Race is a women's only trail running event held in Fairfield, CT, aimed at promoting trail running among women. Scheduled for April 26, 2025, the race features three distances: a 5K, a 10K, and a 4-hour option for participants to run or walk as many laps as possible on a 5K lo..

Squatchywaska Mountainfest is an exciting trail running event taking place in Ellenville, NY, featuring two challenging courses: a 25K and a 10-mile race. Participants will navigate stunning mountain singletracks, experiencing breathtaking views of the Catskills and the iconic Verkeerder Kill Falls...

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, is a celebrated ultra-running event in Kent, Connecticut, marking its 51st anniversary. Known as the oldest 100K race in the United States, it features three race distances: 100K, 50 miles, and 50K, all set on scenic, primar..

Leatherman's Loop is a popular 10k trail race held annually in Cross River, NY, attracting participants of all ages. The event emphasizes community and outdoor activity, taking place in a scenic park setting. Due to its popularity, entry is determined through a lottery system.The registration fee in..

The Forgotten Forest Ultra Run, taking place in Stratford, CT, is a unique 9-hour trail running event set in the scenic Roosevelt Forest. Participants can choose to run, jog, hike, or walk on a well-marked loop trail featuring an elevation gain of approximately 131 feet per loop. This friendly compe..

The Bear Mountain Trail Challenge is an exciting running event set in Bear Mountain State Park, located just an hour from New York City. Participants can choose from three race distances: a 50K, a half marathon (21K), and a 10K. The course features a diverse range of terrains, including short climbs..

The 7 Sisters Trail Race is an exciting running event that features a series of wave starts based on anticipated finish times, ensuring a well-organized experience for participants. Runners are required to carry their own water, as the race is cupless, promoting sustainability. The event is capped a..

The Dandelion Dash and Mushroom Mile is a fun running event taking place in Hadley, MA, featuring a 5K trail run or walk and a 1-mile race suitable for participants of all ages. Scheduled for May 4, 2025, the event aims to support The Hartsbrook School's unique programming, which includes land stewa..

The Blue 2 Blue Challenge is a demanding 50K trail race set in New Haven, Connecticut, known for its challenging terrain and technical trails. Participants will navigate some of the toughest trails in the state, including the Regicides and Quinnipiac Trails, with a total elevation gain of approximat..

The Breakneck Point Trail Runs, organized by Red Newt Racing, is a challenging trail running event set to take place on May 4, 2025, in Beacon, NY. Participants can choose between a half marathon (13.1 miles) and a full marathon (26.4 miles), both featuring significant elevation gains and technical..