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Built on an alfalfa field in 1954 by original founder Ben Segal, the original Oakdale was part of the "theatre-in-the-round" craze that saw many circular stages open in various parts of the Northeast. In the 60s, Oakdale evolved into a summer concert venue where the likes of Harry Belafonte, Paul Anka, Steve & Eydie, Tom Jones, and more played to the open air crowds every summer, sometimes for 2 weeks at a time! The landscape changed in the late 60s and Oakdale rocked and rolled with Cream, The Who, The Doors and even Led Zeppelin, all playing live on the spinning stage.
The 60s and early 70s was the heyday for Oakdale. The wood dome was erected in 1972 and the seating capacity was increased from 1700 to 3200. The biggest entertainers of the day made Oakdale a must play on their summer rosters. Keep in mind: this was prior to the arenas that opened in Hartford and New Haven, and decades before casinos! Staples every summer were Engle Bert Humperdinck, Liberace, The Carpenters, Dolly Parton and comedians like Don Rickles and Rich Little.