Join Us at the Josh

It’s less than a month away, and most of us at Tableaux Wealth are training, or thinking about starting to train, for the 48th annual Josh Billings RunAground Triathlon, happening on Sunday, September 14.

We josh you not. Although it’s our first year as a Tableaux team, most of our team members—cyclist Luke Delorme, the paddling team of Matt and Catherine Chester, and runner Kyle Bean—have participated individually for many years.

© 2025 Josh Billings Runaground Triathlon.

The Josh is one of the oldest continuously running triathlons in the nation, dating back to the late 1970s. Like many of its generation of triathlons—the Outdoorsman Triathlon (1976) and the discontinued Eppie’s Great Race(1974)—the Josh’s bike-paddle-run format is different from the now classic swim-bike-run format.

The race begins with a 27-mile cycling leg at 8:30 AM in Great Barrington, continues with a 5-mile kayak/canoe/stand-up paddleboard circuit in Stockbridge Bowl, and ends with a 6.4-mile run around the Bowl, finishing at Tanglewood’s main gate, where a post-race bash will continue in the east lot until 3:30 PM.

G. M. Baker, November, 1869, 149 Washington Street, Boston, Public domain, via Wikimedia Commons

Lanesborough native Josh Billings (born Henry Wheeler Shaw) was a journalist and writer in the mid- to late-1800s. As a humorist and lecturer he was at least as popular as his contemporaries Mark Twain and Petroleum V. Nasby. He coined the phrase “the squeaky wheel gets the grease” and the aphorism adopted by the race as its motto: “to finish is to win.”

By that definition, we’ll be winners, albeit with a few squeaky joints. We hope to see you there, too.