Trail Running calendar near Great Barrington 2024-2025

The Tower Tag Challenge is an exciting running event taking place at Sleeping Giant State Park in Hamden, CT. Participants can choose between 8-hour and 4-hour options, racing along the Tower Trail, which features a scenic ascent to the Observation Tower. Each loop covers approximately 3.4 miles, wi..

The Frosty Forest 5K is a unique trail running event taking place in Roosevelt Forest, Stratford, CT. This festive race encourages participants to embrace the holiday spirit by dressing in costumes while enjoying the natural beauty of the trails. Runners, joggers, hikers, and walkers are all welcome..

Seth's Fat Ass 50K is an exciting running event taking place in Springfield, MA, at Forest Park. Participants can choose to complete one, two, or all ten loops of the 50K course, with a total time limit of seven hours to finish. The event promises a fun atmosphere and includes custom schwag for all ..

The West Rock Winter Fat Ass Extravaganza is an exciting running event held in Hamden, CT, featuring 1.6-mile loops around Lake Wintergreen for a duration of eight hours. Participants can enjoy a variety of refreshments, including pizza, soup, and snacks, while an aid station provides essential supp..

The Dar Snowshoe Scramble is a fun and low-key running event that offers participants the option to snowshoe or trail run, depending on snow conditions. The course is approximately 3.8 miles, with potential variations between 5k and 10k. The event emphasizes enjoyment over competition, with no forma..

The Frigus Snowshoe Festival, organized by the Endurance Society, is an annual winter sports event held at Moreau Lake State Park in Gansevoort, NY. Scheduled for February 1, 2025, the festival features a variety of race distances, including a challenging 60K ultramarathon, a 30K, a 15K, a 4.7-mile ..

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, at Bigelow Hollow State Park. Revived in 2022 after a hiatus, the race maintains a low-key atmosphere and a friendly community vibe. Participants navigate a scenic course along the Nipmuck Trail, with minima..

The Sleeping Giant Trail Runs is an exciting and challenging trail running event set in Hamden, Connecticut, featuring two race distances: a 25K and a 50K. The course showcases the diverse terrain of Sleeping Giant State Park, with over 30 miles of trails that include smooth carriage roads and techn..

Big Bear Squatch North is an exciting trail running event set to take place in Bear Mountain, NY, featuring a variety of distances ranging from 5K to 50K. The course has undergone several reroutes in previous years due to storm damage, particularly from July 2023, which has affected trail accessibil..

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..

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 Verkeerder Kill Falls. The event ..

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, is a celebrated ultra-running event marking its 51st anniversary, making it the oldest ultra in Connecticut and the first 100K in the U.S. Participants can choose from three distances: 100K, 50 miles, and 50K, all set on a s..

Leatherman's Loop is a popular 10k trail race held annually in Cross River, NY, attracting participants of all ages, from 7 to 107. The event is scheduled for April 27, 2025, and features a lottery system for entry due to its high demand. The registration fee includes the park's entry fee, streamlin..

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 held at 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 terrain, including short climbs..

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 ..

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 Dandelion Dash and Mushroom Mile is a community running event taking place in Hadley, MA, featuring a 5K trail run/walk and a 1-mile fun run. Scheduled for May 4, 2025, the event aims to engage participants of all ages, promoting outdoor activity and family involvement. Proceeds from the event s..

The Ansonia Trails 5K is a running event taking place in Ansonia, CT, designed for participants of the 169 Society. This second annual race features a unique course consisting of two laps around a 1.55-mile loop, making it slightly over or under a traditional 5K distance. Limited to 50 runners, the ..