Like George Washington, Frank Sinatra made many forays into New England over his long career. Unlike George Washington, Sinatra came to sing, dance and campaign for Democratic politicians (Washington was a Federalist).
Sinatra’s periodic visits to New England punctuate a generation of political, cultural and economic changes.
As a young crooner, Frankie Sinatra caused so much pandemonium among his bobby soxer fans that the management of the Boston Armory had to bolt down the seats. As a middle-aged superstar, he hosted his friend John F. Kennedy’s pre-inaugural ball. As an old man, he croaked his way through his old standards at the Worcester Centrum and the Hartford Civic Center.
Frank Sinatra, Crooner
In December 1943, girls stood in line before 8 am to hear 28-year-old “Frankie Swoonatra” at the RKO Boston Theatre. They started screaming before Sinatra showed up because a sailor approached them with a white rat in his pocket. The police had to restore order before the girls could go to the matinee.
Sinatra around 1943
The next month, Frank Sinatra sang again at the RKO Theatre in front of Jan Savitt and his Top Hatters. Frank, Jr., came into the world as he sang his hit songs, like All or Nothing at All, Sunday, Monday and Always, and People Will Say We’re in Love.
Two girls from Chelsea, Mass., started a national Frank Sinatra fan club after listening to his Wednesday night radio broadcasts. . “We aren’t the shrieky kind,” said President Marie Delaney. She said they did constructive things such as sending money to a Chicago orphanage and mailing movie magazines to England.
Just before the presidential election in 1944, Sinatra and Orson Welles appeared at Fenway Park to rally for Franklin D. Roosevelt. Sinatra and Welles brought the house down, according to newspaper reports.
Sinatra with Eleanor Roosevelt, 1960
He was to appear at Symphony Hall in Boston later that month at a sold-out matinee with Arthur Fiedler. The concert was intended to attract a “higher type of audience’ and bring him closer to the so-called ‘concert stage.” Fiedler was to have performed light classics and Sinatra was to have sung popular and standard tunes. Sinatra cancelled at the last minute because he had throat problems.
When Sinatra came to play the Latin Quarter in Boston in 1953, he was on the comeback trail. His career had hit rock bottom. He actually competed for an audience with Frankie Laine, who appeared in the large South Boston nightclub Blinstrub’s Village. The newspaper called it, “The Battle of the Frankies.”
But Sinatra had just finished the film From Here to Eternity, and he’d win an Oscar for it.
Back on Top
By 1956, Sinatra had climbed back on top. By then in his ring-a-ding-ding phase, he starred in the musical film High Society with Grace Kelly and Bing Crosby. Interiors were filmed at a Newport mansion later purchased by Sunny von Bulow. Sinatra and Kelly appear driving together in a scene along Ocean Boulevard in Newport.
Grace Kelly and Frank Sinatra on the set of High Society.
In 1960, Sinatra’s Rat Pack turned into the Jack Pack, as the singer campaigned hard for John F. Kennedy for president of the United States. Sinatra would invite Kennedy to his shows in Las Vegas, bringing him on stage and then back to their hotel suites for parties. On the campaign trail, Kennedy spent two nights at Sinatra’s Palm Springs home. Afterward, Sinatra put up a sign in his bedroom that said, “JFK Slept Here.”
On Jan. 19, 1961, Frank Sinatra and Kennedy’s brother-in-law, Peter Lawford, hosted Kennedy’s pre-inaugural gala in Washington, D.C.
He sang at the Newport Jazz Festival in 1965, nine years after it started, with Quincy Jones and Count Basie. (You can listen to it here). By then his set list consisted of Sinatra classics like Fly Me to the Moon,Luck Be a Lady, In the Wee Small Hours of the Morning and My Kind of Town.
In 1971, Sinatra sang at the eight-year-old Hynes Convention Center in a tribute for Cambridge, Mass.-born comedian Frank Fontaine.
Another Comeback
Frank Sinatra, described once as the patron saint of Italian restaurants, found much to his liking in New England’s many Italian neighborhoods.
In Providence, he liked the Italian wedding soup at Camille’s Roman Garden in Providence. After one pre-concert meal there, he burped on stage. “Excuse me,” he said, “but I just had the most wonderful food at Camille’s Roman Garden.”
On Sept. 5, 1978, he held a press conference in a seafood restaurant owned by an Albanian, Anthony’s Pier 4 in Boston. Sinatra endorsed Kathleen Sullivan Alioto for U.S. Senate from Massachusetts. She was the daughter of Billy Sullivan, owner of the New England Patriots, and wife of San Francisco Mayor Joseph Alioto. His endorsement didn’t help. Paul Tsongas won the nomination and the Senate seat.
President Ronald Reagan awards Frank Sinatra the Presidential Medal of Freedom in 1985
A year later, Sinatra appeared with Dean Martin for unannounced presidential candidate Ronald Reagan — a Republican.
Sinatra made his first New England appearance in the 1980s on Sept. 25, 1981, at the Hartford Civic Center. Four decades after he first sang in New England, he had another hit on his hands: New York, New York. But he wisely began his Hartford concert with I’ve Got the World on a String. He sang the remainder of his New England at large civic auditoriums in Worcester, Providence and Stamford, Conn.
Symphony Hall in Boston
Sinatra once boasted he’d sung in every venue in Boston except Symphony Hall. On Sunday, April 26, 1987, 40 years after he cancelled that concert with Arthur Fiedler, Sinatra finally made it to Symphony Hall.
Francis Albert Sinatra died on May 14, 1998.
This story was updated in 2022.
