WALKING WITH THE CHAIRMAN — The Hoboken Historical Museum’s Self-Guided Sinatra Tour

WALKING WITH THE CHAIRMAN — The Hoboken Historical Museum’s Self-Guided Sinatra Tour

story and photos by Jack Silbert

These vagabond shoes were longing to stray. So I snagged a copy of the Historical Museum’s brochure “Hoboken: The Sinatra Tour,” only setting me back one dollar American.

With Ol’ Blue Eyes’ centennial approaching, it seemed like a very good year to take the tour. In a 1990 letter to the Hoboken Public Library, Frank Sinatra wrote, “I often think back to the days growing up in Hoboken…. singing on a table in my father’s tavern, daydreaming in class at Demerest [sic] High, getting into trouble on the docks… they were pretty exciting times.”

Now I’d be following in his legendary footsteps. Walking all over you, Hoboken, to paraphrase daughter Nancy. Here is my report:


  • Stop No. 1 — 415 Monroe Street
    On December 12, 1915, Francis Albert Sinatra was born here in the family home. (What are you, some sort of fancy lad, born in a hospital?) The house itself is long gone, but there’s an incredibly scuffed-up plaque on the sidewalk. Next door you can still see the awning of the short-lived Sinatra museum “From Here to Eternity.” The museum was the brainchild of former mayoral candidate Ed Shirak Jr. of Lepore’s Chocolates. Mr. Shirak also self-published the Sinatra-themed book Our Way, and wrote and starred in a low-budget musical called “Welcome Home Francis.” And you thought you were a fan.

    (UPDATE: 415 Monroe was completely renovated in 2020, and the star takes center stage…)

  • Stop No. 2 — St. Francis Church, 300 Jefferson Street
    The young Sinatra was baptized here. I like the statue of St. Francis outside the church, because at first you think, “Oh, a couple of birds have landed on it.” And then you realize, no, they are actually part of the statue. But it’s extra appropriate, because — as we learned from the great writer Gay Talese, “bird” was a favorite word of the mid-60’s Sinatra. “How’s your bird?” he might ask, or insist that drinking was “good for your bird.” It was an all-purpose term, like “Smurf” is for Smurfs.

    Hoboken Historical Museum Photo

    Hoboken Historical Museum Photo

  • Stop No. 3 — 333 Jefferson Street
    Sinatra’s folks, Marty and Dolly, opened a bar at this spot named Marty O’Brien’s. (His dad boxed under that name so he could gain entry to Hoboken’s Irish-only gyms.) Not only is the bar long gone; the address doesn’t even exist — it’s been lumped into 461 Fourth Street. So you’ll just have to publicly urinate elsewhere during LepreCon 2016.
  • Stop No. 4 — 530 Jefferson Street
    Sinatra performed here when it was the Crystal Ballroom. The address is now — any guesses? Anybody? That’s right, condos!
  • Stop No. 5 — Sixth and Adams, southeast corner
    This was the location of Tutty’s Bar, and out on the corner, young Frank and his buddies would sing acapella.
  • Stop No. 6 — 354 Sixth Street
    Sinatra was a member of the Weightlifting Club located here. Now it’s the back door of the Nova Dental Center. Just think, his nickname could’ve been Ol’ White Teeth.stop7stanns
  • Stop No. 7 — St. Ann’s Church, 704 Jefferson Street
    In July 1984, Sinatra returned to Hoboken for the first time in nearly 40 years. For decades he’d been a staunch liberal and was still a registered Democrat, but Sinatra was now campaigning with his old friend Ronald Reagan. This took place at the annual St. Ann’s Feast. People who were actually there that day told me they are just now reaching the front of the zeppole line.
  • Stop No. 8 — 604 Grand Street
    Sinatra sang here when it was a social club called The Cat’s Meow. (Now a condo, if you were wondering.) Imagine, if Sinatra worked at a current-era Hoboken spot named The Cat’s Meow, it would be a kitty-sitting day spa with organic kibble.stop9doms
  • Stop No. 9 — Dom’s Bakery, 506 Grand Street
    Even after he’d turned his back on the ’Boke, Sinatra regularly had bread delivered from Dom’s. And that’s way before Seamless existed.
  • Stop No. 10 — Firehouse Engine Co. No. 5, 412 Grand Street
    My own grandfather Herbert Brown loved the fire department almost more than anything. He listened to calls on the scanner, and hung out at his local station house in Flushing, Queens, helping out however he could. When I moved to Hoboken in 1994, the very first thing my grandpa told me: “Sinatra’s dad was a fire captain there.” That was after Marty Sinatra’s boxing days, first a firefighter and then a captain, at Company No. 5. (Now a private home.)Screen Shot 2015-11-29 at 11.59.39 PM
  • Stop No. 11 — Leo’s Grandevous, 200 Grand Street
    This classic Italian spot, established in 1939, has a jukebox crammed with Sinatra classics, and photos everywhere of the Chairman, and why didn’t I do this Walking Tour on a Wednesday when it’s lasagna night here??stop12piccolos
  • Stop No. 12 — Piccolo’s, 92 Clinton Street
    Piccolo’s is equally famous for their rib-eye cheesesteaks as for their Sinatra devotion: the backroom shrine and steady tunes on the sound system. In a 1999 New York Times article, owner Joseph “Sparky” Spaccavento recalled meeting his idol, Frank Sinatra, when Sparky was a teenager delivering for a butcher to Dolly Sinatra. As for Sparky’s son, Pat, who runs the day-to-day operations at Piccolo’s: “I never met Sinatra, but over the years, I got to meet Frank Jr., I met his daughter Tina, I met A.J. his granddaughter,” he explained to me. “We try to keep the legend alive, but I don’t think we have to — I think that will last forever.”stop13observer
  • Stop No. 13 — 111 Newark Street
    As can still be seen from the engraving above the entrance, this building was once home to the Hudson Observer newspaper. It later became the Jersey Observer, and under that title, young Frank briefly worked here as a copy boy, with dreams of being a sportswriter. The Observer eventually merged with the Jersey Journal, and as for Frank, he’d end up spending more time in the entertainment section than the sports pages.stop14cityhall
  • Stop No. 14 — City Hall, 84 Washington Street
    October 30, 1947, was proclaimed “Sinatra Day” in town. At City Hall, he received a key to the city, and then rode up Washington Street in a fire truck driven by his dad. The parade would’ve started earlier, but they had to wait in line in the City Hall basement for 73 hours for a parking sticker.
  • Stop No. 15 — 61 Newark Street
    At the grand Fabian Theater, the teenage Sinatra belted out a tune here. You can relive this great moment by going to this address today and buying some dental floss with your ExtraCare Card.stop16demarestclose
  • Stop No. 16 — Hoboken Charter School, 4th and Garden Streets
    When this was Demarest High (now the Hoboken Charter School), Sinatra spent half a year here before dropping out. Let that be a lesson to you kids: Stay in school or you’ll never amount to anything.stop17library
  • Stop No. 17 — Hoboken Public Library, 500 Park Avenue
    Sinatra concluded that 1990 letter I mentioned earlier by writing, “Congratulations on 100 years of being there, Hoboken Public Library. I may not have spent much time in the building on Park Avenue, but we are all family.” That letter, along with other memorabilia, fills the charming “Sinatra Collection” in a corner of the library’s second floor. And now, as Sinatra himself approaches 100, the library recently celebrated its own 125th birthday. That’s a lot of overdue fees.stop18leporesrangerfrank
  • Stop No. 18 — Lepore’s Chocolates, 105 4th Street
    Back at stop No. 1, I referred to Sinatra superfan Ed Shirak Jr. of Lepore’s Chocolates. Well, the shop is still loaded with Sinatra memorabilia (they count the Sinatra family among their past customers). But there is also an awful lot of New York Rangers memorabilia. And yes, Sinatra wearing Rangers gear. Chairman of the Boards?
  • Stops No. 19 and 20 — 703 Park Avenue and 841 Garden Street
    Walking between these two buildings, where Frank resided at age 12, and then from 13 until 19, I loaded up his 1945 recording “The House I Live In” on my earphones. Because I’m a dork like that.stop21unionclub
  • Stop No. 21 — 601 Hudson Street
    At the Union Club here in 1935, Sinatra performed for $40 a week. Sure, it’s a condominium now (it’s good we’re not playing a Sinatra-sites-gone-condo drinking game). But at least this still looks somewhat like the original building, and is still called the Union Club. History lives!stop22castlepoint
  • Stop No. 22 — Stevens Institute of Technology, Castle Point
    On May 23, 1985, Frank Sinatra made his final public appearance in Hoboken here, receiving an honorary doctorate in engineering. Inspired by his new degree, Ol’ Blue Eyes spent the rest of his waking days hunkered down in a lab, tirelessly crafting a self-aware artificial intelligence prototype. OK, no, I made that up. Sorry, it’s been a long afternoon.stop23skateboardsign
  • Stop No. 23 — Frank Sinatra Memorial Park
    In 1979, a portion of River Road was renamed Sinatra Drive. Then, on July 14, 1998 — two months after his passing — this park was dedicated in Frank Sinatra’s memory. A very fitting spot, I think: On the waterfront where Frank played as a kid, and no doubt marveled at that incredible skyline, thinking, “If I can make it there…”

And a fitting end to the walking tour as well. Considering taking this tour yourself. Also be sure to visit the Hoboken Historical Museum for their comprehensive Sinatra exhibit, on display until next July. And definitely come by the waterfront, stand where Frank once stood — taking in that same unbelievable view — and think a good thought about the local kid who made good. Just remember, there’s no skateboarding allowed in Sinatra Park, or else the ghost of Francis Albert will shatter your kneecaps.

Sinatra Idol in Sinatra Park... in Sinatra's City... in Sinatra's World.

Sinatra Idol in Sinatra Park… in Sinatra’s City… in Sinatra’s World.


Authored by: hMAG