Great Josh Billings RunAground Triathlon

Join us for the Great Josh Billings RunAground Triathlon on September 13, 2026, in Lenox, Massachusetts—a day where families, friends, and nature lovers come together to celebrate community, adventure, and the stunning beauty of the Berkshires. This unique triathlon features a 27-mile bike ride through the rolling hills, a 5-mile paddle across the serene Stockbridge Bowl, and a 6.4-mile run that winds through the historic grounds of Tanglewood, the summer home of the Boston Symphony Orchestra since 1937.

The event kicks off at 8:30 a.m. in Great Barrington, with the bike leg leading participants through picturesque towns and lush forests. The paddle segment offers a peaceful journey across the tranquil waters of Stockbridge Bowl, and the run concludes at Tanglewood’s Main Gate, where the community gathers to cheer on the finishers. Throughout the day, enjoy live music, local food vendors, and family-friendly activities that capture the essence of lakeside living.

Whether you’re a seasoned athlete or a first-time participant, the Great Josh Billings RunAground Triathlon offers an unforgettable experience for all ages. Families can enjoy the Kids’ Fun Run, pet lovers can participate in dog-friendly events, couples can find quiet corners for scenic photo opportunities, and large reunion groups can share meals and activities in the expansive Tanglewood grounds. This event is more than just a race; it’s a celebration of togetherness, connection to nature, and the simple joys of lakeside living. From the sights and sounds of the Berkshires to the tastes and smells of local cuisine, every moment is designed to create lasting memories.

Planning your visit is easy with nearby lodging options available on Lake.com. Remember to bring picnic blankets, folding chairs, and sunscreen to make the most of your day. Ready to make some lakeside memories? Start planning your stay now on Lake.com.