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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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44th Annual Josh Billings Runaground Triathlon Virtual

The 44th Annual Josh Billings Runaground Triathlon will be a virtual event  this year.

Here is what the organizers have to say:

“The first and hopefully only Virtual Josh Billings Triathlon has morphed from a race on Sunday, September 13 to a fundraiser for the Berkshire Humane Society and Berkshire United Way starting on August 15 and ending on September 13.  The goal of the Josh in the year of the COVID-19 virus is to give back to our community and raise as much funds as possible for these two incredible Berkshire organizations.

Here’s the plan: normally the Josh is a 27 mile bike, 5 mile paddle and 6 mile run from Great Barrington to Lenox in the Berkshires.  This year you can bike, paddle and run anywhere (and if you want, swim) as long as you register with a donation of $30 per person which includes a ‘limited edition’ 2020 Josh T-shirt.  We ask that you solicit your community of friends, family and colleagues for $10 or $20 (or more) to raise much needed funds for these very worthy non-profits that do so much for our community.

The link for the Berkshire Humane Society donation page to share with your friends is: 

The link for the Berkshire United Way donation page is:

We would like your participation with all activities to be as safe as possible so we will not be soliciting or recording any times on your chosen course. Please help us discourage unsafe behavior by adhering to appropriate laws or regulations while cycling, running, paddling or swimming in addition to following all current protocols related to COVID-19.

In the spirit of the Josh, join us to bike, paddle, swim and run to support these two essential Berkshire community organizations.

  • Register on (access through the Register Online page on the Josh website) as a team or an ironperson to do all three events or register as an individual to do just one event or any event of your choice. The cost is $30 per person which includes a T-shirt.  You will select which organization you want to receive your donation.
  • Bike, paddle, swim and/or run anywhere and, you can do it over multiple days.  Note: there is no access to Camp MahKeeNac until after Labor Day.
  • Post a picture of your Josh activity on the Josh FB page or Humane Society or Berkshire United Way FB pages.
  • Solicit even more money using social media and email.  Here are the links to the Berkshire Humane Society and to the Berkshire United Way  donation pages.
  • T-shirt pickup will be at the Berkshire Humane Society after September 13 or your T-shirt can be mailed for a small fee.  More information will come later about T-shirt pickup.
  • If you have already registered for the Josh, send an email to to request a refund, to roll over your entry to September 19, 2021, or to make your entry fee a donation to either organization.  Please include your name, phone number and your address if you sent a check.”
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