Josh Billings RunAground

The Great Josh Billings RunAground Triathlon is a cherished annual event that brings together families, friends, and athletes for a day of adventure and camaraderie in the picturesque Berkshire Hills of Massachusetts. This unique triathlon features a 27-mile bike ride, a 5-mile paddle around the serene Stockbridge Bowl, and a 6.4-mile run culminating at the iconic Main Gate of Tanglewood in Lenox. The event is a celebration of athleticism, nature, and local culture, offering participants and spectators alike an unforgettable experience.

The 49th Great Josh Billings RunAground Triathlon is scheduled for Sunday, September 13, 2026, in Great Barrington, Massachusetts. The day kicks off at 8:30 AM at the Barrington Plaza, where participants embark on the scenic 27-mile bike leg through the charming towns of Alford, West Stockbridge, and Stockbridge. The paddle segment follows, with a 5-mile circuit around Lake Mah-Kee-Nac, also known as Stockbridge Bowl, offering tranquil waters and stunning views. The final 6.4-mile run winds through the historic grounds of Tanglewood, leading to the Main Gate in Lenox. The day concludes with “The Bash,” an after-party and awards ceremony at Tanglewood, featuring live music, local food vendors, and a celebration of the day’s achievements.

This event is perfect for families seeking a day of outdoor fun, pet lovers looking for dog-friendly activities, couples desiring a romantic lakeside setting, and large reunion groups eager to share meals and group activities. The triathlon offers a unique blend of athletic challenge and community spirit, set against the backdrop of the Berkshire Hills’ natural beauty. Whether you’re participating or cheering from the sidelines, the Great Josh Billings RunAground Triathlon promises a day filled with togetherness, connection to nature, and the simple joy of lakeside living. Ready to make some lakeside memories? Start planning your stay now on Lake.com.