Hoboken-“My Kind Of Town”

“Give me whatever Frank used to drink” I told the bartender at a cocktail joint Sinatra was known to frequent. With no hesitation he filled a highball glass with ice and then poured Jack Daniel’s to the rim. “This is Frank’s drink” he replied as he placed the drink on a napkin with Sinatra’s photo emblazoned on the top. He recounted a story of Frank punching a bartender in the nose for adding coke to his drink. That sounded like a typical Sinatra legend.

Sinatra’s Drink Photo: Bill Wiatrak

Stories about “the Hoboken kid who got all the breaks” abound, and I’m a big enough fan to know that I needed to stop in the town where Frank grew up and see how much Sinatra’s history had survived. Hoboken lies on the other side of the Hudson from Manhattan and is connected by the Lincoln tunnel. I found an Airbnb within walking distance and started exploring.

A Barbershop in Hoboken Photo: Bill Wiatrak

In Hoboken, I felt like I had stepped back in time. The perfectly maintained vintage homes, clean streets and storefronts seemed untouched by the 21st century.. Even the locals seemed to walk around as if they were part of an elaborate filming location. There was clearly a tangible peace and innocence that I didn’t feel at all on the other side of the tunnel.

Fiore’s! A Legit Italian Deli Photo: Bill Wiatrak

My first stop was to grab lunch at the Italian deli almost as famous than the town where it originated. Fiore’s is a 1913 institution in the heart of the city that makes its own mozzarella (they call it “motz”) and only takes cash. I caught a whiff of aged Italian cheeses, olives and sun dried tomatoes the moment i walked through the door. Everyone working there seemed like they were part of the family and did the same job each day, chatting with customers and speaking random Italian words  as they sliced crusty hoagie rolls and piled layers of deli meat so thick that the bread vanished beneath the cold cuts. They offered me a sample of cheese and  roast beef as they carved away on a seemingly endless supply of Italian goodness. It was Thursday, one of the two days of the week that Fiore’s makes their famous roast beef/motz with gravy. Even half of one of these sandwiches is more than a normal person can eat, but it never hurts to try. 

Fiore’s in Hoboken Photo:Bill Wiatrak

There’s not a seating area at the deli, so I took my sandwich to the boardwalk at Sinatra park and sat on a bench in front of the iconic statue. With Manhattan as the backdrop, a bronze Frank stood leaning against a light post looking perfectly poised to burst into song. A cafe called “Blue Eyes” is set on the water as a further tribute to Hoboken’s most famous resident. As I devoured my hoagie, I decided I’d begin my tour at the Hoboken History museum nearby. 

The Frank Sinatra Map Photo:Bill Wiatrak

The museum isn’t much to look at other than some Sinatra memorabilia and baseball history, but it’s worth a quick visit to grab their DIY walking tour map. Starting with the museum as the first stop, the map guides you around the town to all the areas associated with Sinatra’s life. Each site has a historical explanation and photos making the tour impossibly easy. 

The site of Frank Sinatra’s Birthplace Photo: Bill Wiatrak

There’s more than 20 stops on the map, some of them less associated with Frank’s life than others, so prioritizing the sites is a good idea. The Sinatras moved several times, sometimes just around the block from their previous home and several of these houses still exist. The home that Frank gifted to his parents once his career took off, is on the tour. Sinatra’s father was a boxer, turned bar owner, turned fireman and one can still see the fire station where he worked and the former site of his Irish pub. Many of the buildings have been remodeled or completely rebuilt. The home where Frank was born is no longer there, but there’s a plaque commemorating the location. You can also stop into St. Francis, the church where old Blue Eyes got baptized. 

Dom’s Bakery Photo: Bill Wiatrak

Dom’s is an old Italian bakery that the Sinatra’s visited daily to get their bread. It’s another place frim the past  that isn’t concerned about modernizing and shuts down whenever bread runs out or the owner feels like closing. 

Lepore’s Chocolate Photo:Bill Wiatrak

A few blocks away, the Sinatras satisfied their demand for chocolate with Lepore’s Famous Chocolate Shop, another nice stop on the tour. I missed my window of opportunity to buy bread at Dom’s, but I grabbed some chocolate and made my way to Leo’s, my final stop on the tour. 

The Bar at Leo’s Photo: Bill Wiatrak

“Are you Leo”? I asked the bartender knowing full well that such a thing was impossible. To my amusement, he turned out to be Leo’s grandson, a third generation family member who knew everything about the business and had lots of stories to tell about grandpa and Frank. This is the place Hoboken’s come when they want a legit Italian dinner. I ordered the Chicken Sorrento and a Negroni.  It was easy to see why Leo’s had survived the decades after only a few bites. 

Leo’s Jukebox Photo: Bill Wiatrak

The restaurant’s 50 year old jukebox played “New York New York” as I stepped out and headed back to my place.