The Great Josh Billings Runaground

“To finish is to win." - Josh Billings The 49th Great Josh Billings RunAground will be held on Sunday September, 20, 2026. Start time is 8:30 AM at the Barrington Plaza (located at 333 Stockbridge Rd/Route 7, Great Barrington, MA). The 2026 Josh Billings triathlon route will return to one familiar to faithful participants and spectators. The 27 mile bicycle leg will begin in Great Barrington and continue through Alford, West Stockbridge and Stockbridge, concluding at the Stockbridge boat ramp on Route 183. The paddle leg, which includes the use of canoes, kayaks, surf skis and stand up paddle boards, will launch from the Stockbridge boat ramp, circle Lake Mah-kee-nac/Stockbridge Bowl for 5 miles and transition to the running leg at the shores of Camp Mah-Kee-Nac. Runners will finish their 10k leg of the triathlon at the Main Gate of Tanglewood in Lenox. The after party and awards ceremony, referred to as "The Bash", as well as the Kids Race will be hosted at Tanglewood, in close proximity to the finish line. For 2026, there are 39 categories for Teams, Tin competitors and Iron competitors.