Josh Billings RunAground

The Great Josh Billings RunAground Triathlon, a beloved annual event in the heart of the Berkshire Hills, is a testament to the region’s natural beauty and the enduring spirit of its community. Known affectionately by locals and repeat attendees simply as the Josh Billings RunAground, this triathlon is more than just a sporting event; it is a celebration of athleticism, nature, and local culture.

This event is tailored for a diverse audience, including families, athletes, and nature enthusiasts. The core attendees are often seasoned triathletes, but the event also attracts families who come to cheer on participants and enjoy the scenic surroundings. While the focus is on the triathlon, the event’s appeal extends to music lovers, as it concludes at the iconic Tanglewood, the summer residence of the Boston Symphony Orchestra. Notable guests typically include local legends and athletes, as well as the dedicated volunteers and organizers who make the event possible.

The 48th Great Josh Billings RunAground Triathlon will take place on Sunday, September 14, 2025. The day begins at 8:30 AM at the Barrington Plaza in Great Barrington, Massachusetts. The schedule is packed with action, starting with the 27-mile bicycle leg that winds through the picturesque towns of Alford, West Stockbridge, and Stockbridge. This leg concludes at the Stockbridge boat ramp on Route 183, where paddlers take over. The paddle segment involves a 5-mile circuit around Lake Mah-Kee-Nac, also known as Stockbridge Bowl, before transitioning to the running leg at Camp Mah-Kee-Nac. The final 6.4-mile run ends at the Main Gate of Tanglewood in Lenox. Special happenings include the after-party and awards ceremony, known as “The Bash,” which will be hosted at Tanglewood, close to the finish line.

The event unfolds across some of the most scenic landscapes in western Massachusetts. It begins in Great Barrington and traverses through rolling hills and quaint towns, showcasing the beauty of the Berkshire Hills. The lake, Stockbridge Bowl, is a central feature of the paddle segment, offering serene and picturesque views. To get to the event, attendees can fly into Albany International Airport or Bradley International Airport and then use local transportation or drive via highways such as the Massachusetts Turnpike. The setting is renowned for its natural beauty, with the Tanglewood estate spanning 210 acres and featuring historic sites like the Music Shed and Seiji Ozawa Hall.

The Great Josh Billings RunAground Triathlon is a unique and compelling experience that draws people from all over. The event combines the thrill of a triathlon with the enchanting landscapes of the Berkshires. The bicycle leg offers a challenging yet scenic ride through rural roads, while the paddle segment provides a serene and peaceful experience on the lake. The run, which winds through the historic grounds of Tanglewood, offers a breathtaking finish to the triathlon. The after-party at Tanglewood, with its rich cultural heritage and beautiful grounds, is a highlight of the event, featuring live music, local food, and an awards ceremony that celebrates the achievements of all participants.

This triathlon is more than just a race; it is an immersive experience that blends athleticism with natural beauty and local culture. Whether you are a seasoned triathlete, a nature lover, or simply looking for a unique and memorable event, the Great Josh Billings RunAground Triathlon promises an unforgettable day in one of Massachusetts’ most beautiful regions.