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The annual Josh Billings RunAground to take place on Sunday, September 16

PITTSFIELD – The 42nd annual Josh Billings Triathlon will take place on Sunday, September 16. The race starts in Great Barrington and ends at Tanglewood in Lenox, with a 27-mile bike ride, a 5-mile canoe, kayak, or paddleboard sprint, and a 6-mile run.

Josh Billings is the pen name of renowned humorist, Henry Wheeler Shaw, who was born in Lanesboro, Massachusetts on April 12, 1818. Billings’ saying, “To finish is to win,” is the motto of the RunAground and one of the reasons the event was named after him. “The Josh”, one of the oldest and largest bike-canoe-run triathlons in the country, is an event for all ages and abilities and proceeds from the event benefit Berkshire United Way.  Over the past decade, the Josh Billings has contributed over $75,000 to the organization in support of their mission to build a stronger community here in the Berkshires.

“The Josh has always received tremendous support from the Berkshire community, so it was an easy decision to work with Berkshire United Way when I became race director 16 years ago, knowing that the money raised through the Josh would have the greatest impact on people who need support in our community,” said Patty Spector.

“Berkshire United Way is honored to receive proceeds from the Josh. In the spirit of teamwork and community, these funds are invested in more than 30 local agencies to strengthen the Berkshires,” commented Jenn Kerwood, vice president of development at Berkshire United Way.

The Josh Billings RunAground is calling on volunteers to help support its historic race taking place on September 16.  In addition, teams and singles of all capabilities are encouraged to participate. 

The Josh Kids Race, which is open to all children aged 5-12 regardless of whether their parents/guardians are participating in the Josh, will return again this year.  Kids race participants can register ahead of time from 12-3 at the Arcadian Shop on Saturday, September 15 or from 11 a.m. to 1 p.m. on race day at Tanglewood; just look for the Berkshire United Way tent.  All kids race participants must be registered for this free event.

To register or find more information on the Josh Billings RunAground, please visit

Photo courtesy of Brad Herder.