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 he first proposed a three-day festival at the Weymouth Fairgrounds, the final decision was for a two-day Jazz Festival at Pleasure Island, an amusement park in Wakefield, a suburb north of Boston. Its outdoor theater seated about 7,000.

Then came Newport 1960, with the beer-fueled Saturday night riots that led the city to shut down the festival. (All the sorry details are in Burt Goldblatt’s book, Newport Jazz Festival, published by Dial Press in 1977.) Festivals throughout North America felt the repercussions. At Pleasure Island, it meant a strong police presence, including undercover men in the crowd, and a complete ban on alcohol. Wakefield package stores were ordered closed at 7:00. On Saturday night, the Wakefield police even parked some 3,000 cars themselves to make sure the occupants didn’t enjoy a cold one in the car before heading into the theater. The crowd was extremely well behaved. They had to be: when Gene Krupa’s group broke into “Sing, Sing, Sing,” the people who started dancing in the aisles were escorted out of the festival.


As for the music, it was Wein’s usual stable of stars (find a copy of the program here): Ellington, Oscar Peterson, Brubeck, Pee Wee Russell, Dakota Staton, the Four Freshmen. John McLellan in the Traveler wrote that he found the festival “strangely quiet,” with Saturday sets by Peterson, Dinah Washington, and Art Blakey competent if undistinguished. Then, with Ellington finally catching fire in the night’s finale, the police stopped the show.

Richard Hurt wrote in the Globe that it just wasn’t much fun. “What is served up at jazz festivals ain’t necessarily jazz…It seems to be a case of too much and too little. There is too much commercialism, too much regimentation, too much scheduling. There is too little rapport, too little joy in playing from the heart and even, perhaps, too little cigarette smoke and tinkle of glasses.”

McLellan also groused about commercialism, wondering why the likes of Dakota Staton and the Four Freshmen, entertainers who had little to do with jazz, were repeatedly scheduled at jazz festivals. “And that about sums it up,” he concluded. “The same names year after year, festival after festival. Jazz and pseudo jazz.”

“Big jazz”—festival jazz—was in trouble in 1960. Musically, shows lacked adventure and fresh faces. Socially, communities worried about the prospects of rampage and riot. Financially, Newport was mired in lawsuits, and festivals in five other cities flopped that summer.

The Jazz Festival at Pleasure Island did not flop financially; there were no beer sales, but the festival was at near-capacity both nights. Still, subsequent conversations discussed security measures, not music, and no one in Boston talked about a jazz festival in 1961. In fact, no one talked about a jazz festival again until 1966.

How about a tune that’s as upbeat as this festival report is glum? Dinah Washington was a singer of hits in 1960, but a few years earlier she took some chances with Clifford Brown and Clark Terry, and here’s “I’ve Got You Under My Skin” from those sessions.