On December 12, 1915, in a cold-water flat in Hoboken, a young Italian woman gave birth to a little baby boy with the most beautiful blue eyes the world would ever see. And his voice didn’t turn out to be too shabby, either. Frank Sinatra’s pipes went on to put both him, and the small town of Hoboken, on the map. Today, we revisit some famous Sinatra haunts.
A city of immigrants just starting out in America, Hobokenites all felt a sense of possibility in seeing Sinatra’s name in lights. While Ol’ Blue Eyes didn’t always hold his hometown in the highest regard, a few local places drew him back to the square mile where he found his feet (and his voice).
In honor of Sinatra’s 100th birthday on December 12, take a visit to New Jersey, 07030, and check out some of his beloved haunts — including a few that are now veritable shrines to the guy from the neighborhood who made it big in Hollywood.
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Sinatra’s Childhood Home
Address: 415 Monroe Street
In Sinatra’s time: Frank Sinatra was born and raised in this four-story, cold-water tenement building, at 415 Monroe Street. Located in the Italian section of Hoboken — apart from the German-Irish section — Sinatra grew up on the “wrong” side of the tracks in a town where Italians were the underdogs in society.
Today: Sinatra’s childhood home burned down in the late 1960s, but visitors can still check out a brick archway and a commemorative star in the sidewalk, both honoring The Chairman of the Board.
St. Francis Church
Address: 308 Jefferson Street
In Sinatra’s time: Nearly 100 years ago, on April 16, 1916 this Catholic church was the site of the baptism of one Francis Albert Sinatra. St. Francis was built in 1888 as a place for Italian immigrants, new to both American and the English language, to go for worship services and confession in their own native tongue.
Today: You know you’re at the right spot when you see the statue of St. Francis on the corner (pictured). You can still attend mass at St. Francis, and, if you’re feeling very in touch with Sinatra, there’s even a traditional Italian mass on Sundays at 11 a.m.
Dom’s Bakery Grand
Address: 506 Grand Street
In Sinatra’s time: The bread from Dom’s Bakery had a special place in Sinatra’s heart. Like any good Italian boy, he knew good bread, and wouldn’t settle for anything less than the real stuff. Even when he moved out to California, Sinatra famously had Dom’s bread delivered weekly to his home on the West Coast.
Today: Visit Dom’s any day of the week for arguably the best bread in Hoboken (and possibly the world). If it’s good enough for Sinatra, it’s good enough for me!
St. Ann’s Church
Address: 704 Jefferson Street
In Sinatra’s time: Rumor has it that Sinatra made his singing debut at St. Ann’s ravioli dinner back when he was just a boy. Flash forward to 1984, when Sinatra visited here with Ronald Reagan for the church’s annual feast — which was his first public appearance in Hoboken in more than 30 years — and turned out to be one of the last appearances he would ever make in his hometown.
Today: St. Ann’s is still a thriving parish, and draws a huge crowd for its annual St. Ann’s Italian Festival each summer (pictured).
Leo’s Grandevous
Address: 200 Grand Street
In Sinatra’s time: Like many in Hoboken, owners Leo and Tessie DiTerlizzi were avid supporters of the singer — and Leo was reportedly a school mate of Sinatra, who frequented the restaurant. Photos of Ol’ Blue Eyes lined the walls, and his music played throughout the dining room. Leo’s proudly showed its appreciation for Hoboken’s favorite son as he won over the world with that voice.
Today: Leo’s is still just as devoted to The Chairman of the Board as it always has been. Said to have “The World’s Greatest Frank Sinatra Jukebox”, and voted one of the “50 Greatest Bars in the United States” by GQ, Leo’s is the place to go for a delicious meal and jukebox that only plays Sinatra’s tunes. Leo’s is pulling out all the stops for Sinatra’s 100th birthday, including live entertainment and reservation-only seatings for the truly faithful fans. Email Grace at Leosgrandevous@optonline.net or call 201-659-9467 if you’d like to take part in this authentic celebration of Sinatra’s life and music.
Piccolo’s Famous Cheesesteaks
Address: 92 Clinton Street
In Sinatra’s time: Much like Leo’s Grandevous, Piccolo’s is the product of some very hardworking Italian-Americans. Owner Joseph “Sparky” Spaccavento opened Piccolo’s Clam Bar in 1955, which served the namesake shellfish — as well as hot dogs, hamburgers and cheesesteaks. And yes, Sinatra reportedly ate at Piccolo’s back in the day
Today: A small, one-story building sandwiched between two larger apartment complexes, Piccolo’s is now known for cheesesteaks and its Sinatra connection. The restaurant plays Sinatra’s music every day, and photos of the singer adorn the walls.
A.J. Demarest High School
Address: 158 Fourth Street
In Sinatra’s time: Sinatra was famously kicked out of high school in his freshman year for misbehavior. As childhood friend Tony Consiglio wrote in his book Sinatra and Me: The Very Good Years, the Chairman of the Board got expelled for releasing pigeons during a play put on by his classmates.
Today: Following the construction of a new high school building, Demarest High School was converted into strictly a junior high school and is now known as A.J. Demarest Middle School.
The Union Club
Address: 600 Hudson Street
In Sinatra’s time: This popular, Italian-owned banquet hall saw Sinatra perform for $40 per week back when he was first getting his start in the mid-1930s, until he started to garner some success in 1938. Sinatra returned sometime around 1950 for a performance that left the singer feeling disrespected by the people of Hoboken. He left the stage and vowed to never make another appearance in Hoboken again, a promise he kept until his 1984 trip to St. Ann’s Italian Festival with Ronald Reagan.
Today: The Union Club is no longer the banquet hall that saw so many Sinatra performances, but has since been converted into condominiums. It’s still worth a trip by for anyone who truly wants to walk the streets that Sinatra traveled down when he was making his start.
Lepore’s Home Made Chocolates
Address: 105 Fourth Street
In Sinatra’s time: Lepore’s Home Made Chocolates has been a staple in Hoboken since 1980. Sinatra himself would stop in to pick up his beloved chocolate-covered apricots — or send his limo driver if he was feeling extra Hollywood at the moment.
Today: Lepore’s still serves up delectable desserts (including Sinatra’s favorite apricot treats) to the neighborhood. Owner Ed Shirak is an avid Sinatra fan and displays photos and memorabilia throughout the shop.
Joseph F. Brandt School
Address: 215 Ninth Street
In Sinatra’s time: This is the spot where little Frank got his start in education. He displayed no interest in school (and apparently no talent for it either). Luckily for him, he was decent at a few other things.
Hero (Top) Feature Image: © Wikimedia Commons
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