Sinatra in Hoboken

415 Monroe Street – Sinatra’s Childhood Home

This is where Frank Sinatra was born and spent his childhood until he turned 12. The Sinatras lived in a cold-water tenement building at 415 Monroe Street until 1927. It was a poor section of town settled by Italians (the more prestigious German-Irish section was located east of Willow Street.) The four-story multifamily building no longer exists – it burned down in the late 1960s. Now it’s marked by a Bronze Star, installed in 1996 by the Hoboken Historical Museum.

308 Jefferson Street – St. Francis Church

Sinatra was baptized at St. Francis Church by his Godfather, Frank Garrick. The baby was supposed to be named Albert, but when the bishop asked his godfather, Frank Garrick, what ‘his’ name was, he answered “Frank,” not understanding that the question was about the baby’s name.

St. Francis Church was built in 1888 as a place of worship for newly arriving Italian immigrants, most of whom had difficulties with the English language. It’s still an active community parish and still offers Sunday mass in Italian.

333 Jefferson Street – Site of Marty O’Briens

Here stood a bar that belonged to Sinatra’s parents, Marty and Dolly. Marty Sinatra was a prizefighter and boxed under an Irish pseudonym – Marty O’Brien, because of the discrimination towards Italians. He named the bar Marty O’Brien’s after his boxing persona. Here, in Marty O’Brien’s, young Sinatra practiced his singing chops.

704 Jefferson Street – St. Ann’s Church

Sinatra visited here in 1984 with Ronald Reagan. It was his first public appearance in Hoboken in more than 30 years — and turned out to be the last one. St. Ann’s is still a functioning church.

412 Grand Street – The Firehouse Engine Co. No.5 

After his boxing days were over, Marty Sinatra served here as a firefighter and later as a fire captain at this firehouse. The resourceful and well-connected Dolly Sinatra undoubtedly helped Marty get a prestigious fireman job. Now, this building is a private residence.

506 Grand Street – Dom’s Bakery

Sinatras used to get all of their bread from Dom’s Bakery. Frank Sinatra considered it the best bread in the world, and even after he became a huge star and left town, he had Dom’s bread delivered to his home in California. The bakery, which was in business from the early 1900s, closed its doors in January 2023 when its owners retired after 43 years.

604 Grand Street – Site of Cat’s Meow

In the mid-1930s, when young Sintra was an aspiring singer looking for opportunities to perform, the Cat’s Meow – a local Hoboken social club – not only offered him a stage but also an occasional opportunity to sleep under the pool table when he wanted to get away from his mother.

200 Grand Street – Leo’s Grandevous

The restaurant opened in 1939 when Sintra was on the brink of becoming a star. The restaurant’s owners, Leo and Tessie DiTerlizzi, were avid Sinatra admirers. Leo was his personal friend and closely followed Sinatra’s early career, attending all his shows and showing much support. Sinatra still lived in Hoboken when the restaurant opened and reportedly liked to come here for food and drink.

The restaurant feels like a shrine to Sinatra, with tons of Sinatra’s photos, posters, and memorabilia. Still a lively local spot, it serves an Italian fair and features an old-fashioned jukebox with many of Sinatra’s selections.

703 Park Ave – Sinatras’ second home

The Sinatra Family moved to 703 Park from 415 Monroe Street in 1927. Frank’s father, Marty Sinatra, landed a job as a firefighter, which helped the family move into a better building in a more prestigious German/Irish part of town. This apartment building with bay windows and patterned brick was a huge step up for the family. It still stands as a residential apartment building.

841 Garden Street – Sinatra’s teenage home

The next move was even more significant. With each relocation, Sinatra’s ambitious and socially active mother moved the family further eastward and northward to better and more prestigious parts of town. Not only that but they upgraded from an apartment to owning a whole house. This was Frank Sinatra’s home when he was a teenager, and he even had his own room on the top floor. Sinatras had a baby grand piano in the living room and a gold-and-white telephone. The family moved here in 1928 when Frank Sinatra was 13, and he stayed here until 1939 when he married Nancy and left Hoboken for good. It’s still a private house.

600 Hudson Street – The Union Club

Until World War I, the city’s demographics was dominated by German immigrants who formed a social club called The Deutscher Club and, in 1870, constructed a two-story building at 600 Hudson Street to house it.

In the 1930s, a local Italian businessman purchased the building and renamed it The Union Club. The venue was quite posh, with three bars, a wine room, a “Gold Room” for female patrons, and a ballroom with a stage. This is where Frank Sinatra landed his first regular gig for a whopping $40 a week.

The building is almost unrecognizable from its club days and is now a condo.

909 Hudson St – Sinatra’s gift to his parents

Frank Sinatra bought this beautiful house in the most prestigious part of town for his parents, Marty and Dolly, when he became a big band singer. They lived in this house until 1956, when they left Hoboken for good.

Demarest High School on 4th and Garden – Sinatra’s High School

Sinatra attended Demarest High School for only half a year before dropping out, to the great disappointment of his parents. Now, the building houses Hoboken Middle School.

215 Ninth Street – Joseph F. Brandt Primary School

Sinatra’s elementary school. Living and breezing, it changed its name but is still a functioning school.

340 Sinatra Drive – Frank Sinatra Statue

The statue of Hoboken’s favorite son was dedicated on what would have been his 106th birthday, December 12, 2021. Sculpted by Carolyn Palmer, Frank Sinatra is wearing a suit and tie and beaming his famous happy smile.

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