Great Josh Billings RunAground Triathlon

The Great Josh Billings RunAground Triathlon is one of the oldest triathlons in the United States, second in longevity only to Eppie’s Great Race in California. It has been held in Southern Berkshire County, Massachusetts, every year since 1976, and it is not what most people picture when they hear the word triathlon. The race is named after 19th-century humorist Josh Billings, whose philosophy — “To finish is to win” — has become the event’s permanent motto. No one here is chasing the podium. What they are chasing is a 27-mile bike ride through the Berkshire Hills, a 5-mile canoe or kayak sprint across Stockbridge Bowl, and a 6-mile run that finishes in the shadow of Tanglewood, summer home of the Boston Symphony Orchestra since 1937. Roughly 2,000 participants and spectators gather each September to watch one of New England’s most distinctive race weekends unfold across some of its most rewarding landscape.

Bike, Paddle, Run: The Berkshire Way

The race begins in Great Barrington, where the bike leg sends riders through the rolling towns of Alford, West Stockbridge, and Stockbridge before hitting the climb that locals have been dreading and loving in equal measure for fifty years. The ascent of Prospect Hill in Stockbridge is where the race separates itself from a pleasant countryside ride — spectators line Route 102 near the Red Lion Inn in Stockbridge to watch cyclists take the sharp left turn up the hill, which offers the best roadside view of the course. From the hilltop descent, riders reach the Interlaken boat ramp on Stockbridge Bowl — a clear, spring-fed lake ringed by the Berkshire Hills — where paddlers wait with canoes and kayaks for the transition. The 5-mile paddle across the Bowl is the race’s defining segment: open water, a light September chop, and the sound of the BSO’s summer season behind you. The run begins at the far shore and winds to Tanglewood’s Main Gate, where the finish-line crowd fills the lawn as teams cross in all conditions and all forms of exhaustion. The post-race gathering at Camp Mah-Kee-Nac, near the finish area, is where teams recover, eat, and compare notes on which hill hurt most.

The Berkshires Beyond Race Day

The Stockbridge Bowl itself is one of the prettiest bodies of water in New England and rewards a morning paddle or kayak rental before or after the race. Tanglewood’s grounds are open to the public outside of performance dates, and the main lawn is a legitimate destination for families with a picnic blanket and an afternoon to spend. In Lenox, Nudel Restaurant on Church Street has built a strong regional reputation for its market-driven small plates and handmade pasta — the seasonal risotto and wood-roasted vegetable dishes change with what’s available locally, and the space itself is unpretentious and warm. For breakfast the morning of the race or the day after, Haven Café and Bakery in Lenox opens early and does strong coffee, house-made pastries, and full egg plates that work as pre-race fuel. The Norman Rockwell Museum in Stockbridge, four miles from the Stockbridge Bowl paddle finish, houses the most complete collection of Rockwell’s work in existence and is one of the better family museum experiences in the Northeast — the building’s grounds back up to the Housatonic River, and children respond to Rockwell’s accessible, story-driven imagery with genuine attention.

Practical Notes for Race Weekend

If you are racing, registration opens at joshbillings.com with team formation required well in advance of race day. Teams of three share the three legs; solo or duo entries are also accommodated. Route 183 from Lenox toward the Stockbridge Bowl boat ramp closes to vehicle traffic at 8:30 AM on race day; Hawthorne Road closes at 9 AM and reopens at 12:15 PM. Spectators should plan to arrive at their preferred viewing spot before road closures take effect. Mid-September in the Berkshires averages in the low-to-mid 60s Fahrenheit with morning fog that burns off by late morning — bring a layer for the early start and sunscreen for the paddle. The race runs in nearly all weather; verify any postponement decisions at joshbillings.com the morning of the event.

Good to Know
– The best spectator spot on the bike course is Route 102 near the Red Lion Inn in Stockbridge, before the Prospect Hill climb.
– Paddle teams should confirm canoe or kayak availability through the official race registration process early — equipment can be rented or brought.
– The finish-line area near Tanglewood’s Main Gate is open to non-racing spectators and worth attending even if you have no one in the race.

Berkshire Lake Country on Lake.com

Stockbridge Bowl is the most visible lake in the race, but the Berkshires hold a network of quiet waterways that make a full weekend stay well worth the drive. Onota Lake in Pittsfield, Pontoosuc Lake, and the stretches of the Housatonic River valley all have waterfront rental options within twenty minutes of the race course. Search Berkshire County waterfront options on Lake.com and consider arriving Thursday to settle in before race Saturday. The window between Tanglewood’s summer season close and the fall foliage peak is one of the best-kept seasonal secrets in New England.