The 49th Josh Billings is over!

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Next Josh - September 19th, 2027

Bike

Teams start in Great Barrington, MA and bike 27 miles through 5 towns of scenic back country roads and rolling hills to Stockbridge Bowl in Stockbridge where bikers hand off the wrist band to paddlers waiting at the lake.

Paddle

Canoeists, kayakers and SUP’s sprint 5 miles around the lake ending at Camp Mah-Kee-Nac where the wristband is tossed to runners waiting on the beach.

Run

Runners head out of the camp and run 6.4 miles around the lake and finish at the Tanglewood Main Gate where thousands of friends and family and fans cheer on the finishers.

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Recent Press

Press

July 31, 2026

WTBR-FM’s ‘Morning Drive’ – Guests: Brian Berkel & Chris Calvert

Talking about all things Josh Billings on WTBR-FM's 'Morning Drive' with Brian Berkel & Chris Calvert July 31, 2026 https://pittsfieldtv.org/program/?id=56453

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Press

July 13, 2026

WSBS 94.1 FM Morning show with Jesse Stewart

Listen in on Josh Billings Race Director Brian Berkel with Jesse Stewart on the Morning Show, WSBS 94.1 July 9, 2026 talking about all things Josh Billings.

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