Josh Billings RunAground Triathlon 2021

The 2021 Josh Billings RunAground, is just around corner, scheduled for Sunday, September 19th, 2021. This bike/paddle/run triathlon was first held in 1976 and remains the second oldest, continuous triathlon in the country.

Josh Billings was the pen name of the 19th-century American humorist, Henry Wheeler Shaw (1818-1885). Shaw was a famous humor writer and lecturer in the United States during the latter half of the 19th century whose humorous writings were often compared to Mark Twain’s.

The Josh Billings RunAground Triathlon adopts this fun-loving, only half-serious tone as its own and uses one of Billings’ quotations as its motto: “To Finish is to win.”

Josh Billings Triathlon celebrates its 45th anniversary in 2021, second only to California’s Eppie’s Great Race as the oldest continuously held triathlon in the United States.

A Bike/Paddle/Run Triathlon

While most triathlons are bike/swim/run events the RunAground replaces the swim portion with a paddling challenge.

The event begins with a 27 mile bike race from Great Barrington to the Stockbridge Bowl. The second portion is a 5-mile paddling sprint around the on Stockbridge Bowl. Contestants can use canoes, kayaks, or SUP boards. The last leg of the triathlon is a 6 mile foot race around the Stockbridge Bowl, then down to the finish line at the main gate of Tanglewood, in Lenox.

After the race enjoy The Bash at Tanglewood. Festivities are set to include food and beverage vendors, the Josh awards, and live music: The Everything Else performing The British Invasion Experience.

RunAground Spectating Tips

Josh Billings RunAground Triathlon 2021

The annual Runaground offers as much fun and excitement for spectators as it does contestants. Maybe even more so. That being said, there are a few tips that can make watching race day that much better.

Bike Leg – Race Start at 9:30am
The best place to be at the start of the triathlon is along the side of US-7 in Great Barrington. Be sure to arrive early to acquire a good vantage point before they fill up. The race starts off from in front of the Price Chopper supermarket, less than 15 minutes from our Berkshires bed and breakfast.

Another excellent place to be is on the final turn before the Stockbridge Bowl finish when the cyclists will be giving it their all.

Paddle Leg
The paddle leg of the race involves making 1 and 3/4 laps (5 miles) around the Stockbridge Bowl. Getting a good view during this portion of the triathlon is more of a challenge.

Those without waterfront property-owning friends should consider watching from Camp Mah-Kee-Nac. This location offers excellent lake views, plenty of room to spread-out, and a good vantage to watch the transitions from paddling-to-running. Binoculars are another good idea.

Josh Billings RunAground Triathlon 2021

Running Leg
The final leg takes runners back down and around the Stockbridge Bowl, then back up to Tanglewood’s main entrance.

Interlaken Road offers numerous driveways and intersections for watching the runners as they make their way from the Bowl to Tanglewood.

The hill next to the Kripalu Center property is a great spot to watch and lend encouragement as the runners take the last hill to the finish line. It also puts you conveniently close to the after-party at Tanglewood. And all less than 10 minutes from your room at The Inn at Stockbridge!

2021 Josh Billings RunAground Triathlon

Registration for this year’s event can be done online or in-person on Saturday, September 18th, between 12pm and 5pm, at The Arcadian Shop, 91 Pittsfield Road, in Lenox, MA.

Race Day is Sunday, September 19th, starting at 9:30am from the Price Chopper parking lot at 300 Stockbridge Road, in Great Barrington, MA.

Visit for more information. You can also find the triathlon on Facebook.