The Troy Street Observer

August 26, 1960: Jazz Festival at Pleasure Island

The Jazz Festival at Pleasure Island, held August 26-27, 1960, was the last of Boston’s big outdoor festivals, following the North Shore Jazz Festival in 1957 and the Boston Jazz Festival in 1959. Pleasure Island was sometimes called the Second Boston Jazz Festival, mainly because PAMA, George Wein’s new company, produced it. Wein might have been at the helm, but circumstances had changed since August 1959.

Ad for the Jazz Festival at Pleasure Island
Newspaper ad for the Jazz Festival at Pleasure Island, August 1960

The Boston Jazz Festival had not been a financial success, and Wein planned changes for 1960. He had a suburban location in mind (think “parking”), and though a three-day festival at the Weymouth Fairgrounds was proposed, the final decision was for a two-day affair at Pleasure Island, an amusement park in Wakefield. Its outdoor theater seated about 7,000.

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