The Sinatra Walking Tour: Hoboken Through Ol’ Blue Eyes Himself

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When most people think about Hoboken they think of Ol’ Blue Eyes — Frank Sinatra, the “kid from Hoboken who got the breaks,” as writer Bruce Bliven coined him. All over the Mile Square, tributes pay homage to this musical and historical legend, as Hoboken was his birthplace and where he found his fame. The city is decorated with all things Sinatra from restaurants to landmarks that feature all parts of his life.

Thanks to the Hoboken Historical Museum, we have been able to put together a Frank Sinatra Walking Tour around Hoboken to see all of the significant locations that played a huge role in shaping him into the man he once was. Keep reading for all the spots to check out on a Sinatra walking tour to see Hoboken through ol’ Blue Eyes himself. 

The Stops 

Stop No.1: 415 Monroe Street

First on the list is 415 Monroe Street, a cold water flat where Francis Albert Sinatra was born on December 12th, 1915 to immigrant parents Natalia Della Garaventa {known as Dolly} and Antonino Martino {“Marty” — explanation to follow} Sinatra. The building was torn down in 1970 but the legacy lives on in the spirit of the town. Fun fact: Sinatra weighed over 13 pounds at birth. He was delivered using forceps, which caused permanent damage to his face and ear. 

Stop No.2: St. Francis Church

st francis sinatra

^Sinatra with his mom at St. Francis Church

{Photo credit: Hoboken Historical Museum}

Sinatra was baptized at St. Francis Church, located at 300 Jefferson Street, on April 2nd, 1916 by his Godfather, Frank Garrick. This church continues to serve the Roman Catholic community of Hoboken and holds strong to their Italian roots, offering mass in Italian on Sundays. Despite his many divorces, marriages, and quarrels, Frankie remained spiritual throughout his life.

Stop No.3: 333 Jefferson Street

Next on the list is 333 Jefferson Street, where his parents, Marty and Dolly, owned a bar and grill called Marty O’Briens. Sinatra’s father went by the name Marty O’Brien during his boxing days because of the large Irish population in the area. He named this spot after his boxing persona and Marty O’Brien’s continues to be an iconic name throughout the city and once was a bar on 1st and Bloomfield. Sinatra used to sing here quite a bit in his day and his presence always drew a large crowd.

Read More: A Hoboken Walking Tour: A {Literal} Step Into The Past

Stop No. 4: Tutty’s Bar

Tutty’s Bar { at 610 Adams Street}, which is now a residential area of Hoboken, was best known for being the spot where Sinatra and his friends would gather. They would hang on the corner and he would sing a capella. Imagine witnessing an impromptu Blue Eyes concert back in the day — total swoon. 

Stop No. 5: 354 6th Street

Continuing on 6th Street, towards 354 6th Street, was the Jefferson Hall and Weightlifting Club. Sinatra joined this club during the Great Depression. He paid $1.00 per month for membership. Nowadays, gym go-ers can’t even buy a bottle of water for that amount. 

Stop No.6: St. Ann’s Church

st anns church

The iconic St. Ann’s Church {at 704 Jefferson Street} still holds mass to this day and continues to host the most visited Italian festival in the area. It was here where Sinatra introduced President Ronald Regan during his campaign trail in 1984. The gathering took place in the church gym where they ate and mingled with fellow Hobokenites over ravioli and sauce. 

Stop No.7: Dom’s Bakery

Hoboken’s most well-known gem is Dom’s Bakery at 506 Grand Street, where Sinatra and his family used to get all of their bread. Even after Sinatra left town, he would always return back home for the best bread in Hoboken {and the world, for that matter}.

Stop No. 8: The Firehouse Engine Co. No.5 

The Firehouse Engine Co. No. 5 is an important part of Hoboken history as Marty Sinatra served Hoboken as a firefighter and later as a fire captain at this firehouse. This building is now a private residence. 

Stop No. 9: Leo’s Grandevous 

leo's hoboken

Even out of towners know of Leo’s Grandevous at 200 Grand Street and can smell the delicious Italian food from down the block. This was one of Sinatra’s favorite local spots and he ate there often. The restaurant still reserves a chair for him and honors his legacy with pictures and memorabilia adorning the walls. They make some of the best Italian food in Hoboken. 

See More: The Oldest Businesses in Hoboken

Stop No. 10: Jersey Observer Newspaper

Once the Jersey Observer Newspaper, located at 111 Newark Street and, originally named the Hudson Observer, Sinatra worked as a copy boy earning a measly $12 a week. 

Stop No. 11: Hoboken City Hall 

hoboken city hall

Hoboken City Hall at 94 Washington Street is a landmark in and of itself but notably honored Sinatra on October 30th, 1947 when they celebrated Sinatra Day. He was driven up to Washington Street on a fire truck by his father were screaming fans and friends gathered to watch him receive the keys to the city. It was raining that day but that didn’t stop the crowds from being there.

Stop No.12: Hoboken Middle School {formerly Demarest High School}

Sinatra attended Demarest High School on {4th and Garden} for only half a year. During that time, many of his classmates and peers left school. Sinatra followed suit and dropped out. Now, this spot is known as the Hoboken Middle School. 

Stop No. 13: The Hoboken Public Library 

The Hoboken Public Library at 500 Park Avenue has a Sinatra collection that was created in memory of his mother, Dolly, who died in a plane crash in 1977. Check out the library’s Sinatra collection for more information. 

Stop No. 14: 703 Park Avenue

In 1927, the Sinatra family moved to this location. His parents chose here because it was a much wealthier German/Irish part of Hoboken. It continues to serve as a residential location in town and has been renovated since.

Stop No. 14: Joseph  F. Brandt Primary School

The Joseph F. Brandt Primary School at 215 Ninth Street is where Sinatra attended elementary school. He was quite an animated child and always had a stage presence, even at a young age. His mother made sure that he was always well dressed. 

Stop No. 15: 841 Garden Street

The house at 841 Garden Street was the house where the Sinatra family moved in 1932 when Frank was just 17 years old. He had his own bedroom on the top floor of this family home. 

Stop No. 16: 837 Garden Street

The home at 837 Garden Street served as another residence for Dolly and Marty Sinatra. The one-bedroom and one and a half bath brownstone apartment still stands today and currently estimated to be worth $1.8 million on Zillow. 

Stop No. 17: 909 Hudson Street

The house at 909 Hudson Street was the house that Frank bought for his parents after becoming a big band singer. 

Stop No. 18: Stevens Institute of Technology 

The tour ends at Stevens Institute of Technology at 1 Castle Point Terrace, one of the most beautiful views in all of Hoboken where Frank Sinatra was presented with an honorary Doctoral Degree in Engineering. This was awarded to him on May 23rd, 1985.

This list was adapted from the information provided by the Hoboken Historical Museum and is a comprehensive list of major historical sites. There are many more spots where Frank Sinatra left his legacy throughout the city and we invite you to explore that and so much more at the Hoboken Historical Museum.

Have you been to any of the spots on the tour? Let us know in the comments! 

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Hoboken homeowner and lover of all things local, Danielle made her home in the Mile Square City nearly six years ago. Danielle is a second grade teacher by day; after hours, she can be found in the kitchen whipping up a a new recipe or grabbing a bite to eat with her husband and friends. Danielle is the try-er and buyer of all things beauty and loves finding a good deal. Shopping on Washington, interior decorating, and riding her Peloton are just a few of Danielle's favorite things. Oh, and did we mention her undying love for the New York Yankees?