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45th Annual Josh Billings RunAground Triathlon

The 45th Annual Josh Billings RunAground Triathlon will be held Sunday, September 19, 2021 beginning at the Price Chopper parking lot in Great Barrington, MA and ending at Tanglewood in Lenox, MA.

The triathlon is named after a famed 19th Century humorist who lived in the Berkshires. The event reflects Mr. Billings not-too-serious attitude.

The triathlon includes a 27 mile bike, a 5 mile canoe/kayak/SUP (standing up paddleboard) and a 6 mile run.

Due to COVID concerns, the kids race is canceled this year but will return in 2022.

The long-time event is known as one of the largest and oldest Bike/Canoe/Run triathlons in the country. Register early because the popular event has a 500 team capacity. Note that there is no sign up on race day.

Go to: to register for either the in-person triathlon or the virtual version.

This year the Josh Virtual will again support the Berkshire Humane Society.

To learn more about the Berkshire Humane Society visit

Sunday, the race begins at 9:30 am with the biking portion of the triathlon.

The Josh Billings website,, is very comprehensive which is good, because there is a lot to know. There are 44 categories for entrants including iron men, two, three and four-person teams and there are age and gender divisions for each . Check the “Race Categories” section of the website for details.

There are a variety of entry fees as well, depending on your category, but there are three registration deadlines , and the entry fee increases after each. Check the “Registration” section for fees and deadlines. By the way, it pays to be old at the Josh- 70 years and older athletes can compete for free.

The triathlon covers a lot of ground from the Price Chopper parking lot in Great Barrington to the Stockbridge Bowl to Tanglewood. It will take some  planning  to position your team members and equipment. The website explains it all.

The Josh also partners with CrowdRise, which allows participants to fundraise for their own causes while competing in the event.

For any questions that the website doesn’t cover, email Patty at or call (413) 344-7919.

Proceeds from the in -person event will benefit Berkshire United Way in Pittsfield, MA. To learn more about the Berkshire United Way, visit

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