In Frank’s Footsteps: The Sinatra Walking Tour

Monroe Street, between Fourth and Fifth streets in Hoboken, isn’t much to look at. The modest three- and four-story multifamily houses that line the one-way street are faced in a dreary mix of brick and aluminum siding. Little suggests that this is the block where Frank Sinatra came into the world on December 12, 1915. It’s also the first stop on my tour of Sinatra’s Hoboken.

You can pick up a map and guide to the two-hour walking tour at the Hoboken Historical Museum, 1301 Hudson Street. While you are there, check out the museum’s centennial exhibit of Sinatra memorabilia and videos through July 3, 2016. The newly revised tour map starts at the museum, indicates 19 other places of interest and ends at 415 Monroe. I prefer to begin at the beginning, with Sinatra’s birthplace.

Photo by Ken Schlager

Sinatra Birthplace, 415 Monroe Street
The four-story, eight-family building at 415 Monroe Street where Sinatra was born no longer exists. A fire consumed the wood-frame structure in 1967. The city demolished the building the following year. These days 415 Monroe is a private parking lot marked by a crude brick arch erected in the 1970s by the two families who owned the property.

Photo by Ken Schlager

From Here to Eternity
In 1996, the local historical society placed a Hollywood Walk of Fame-style star in the sidewalk near 415 Monroe Street with the inscription, “Francis Albert Sinatra: The Voice.” Today it is scuffed and tarnished; weeds fill the cracks around its edges. The one-story shack to its left briefly served as a Sinatra museum. Its awning still boasts an image of an Oscar statuette and the words, “From Here to Eternity.” (The film earned Sinatra an Academy Award as best supporting actor in 1954.)

Photo by Ken Schlager

St. Francis Church
From Monroe Street, I walk four blocks to St. Francis Church at the corner of Third and Jefferson. (All streets in the neighborhood are named for early American presidents.) This is the church where Sinatra was baptized Francis Albert on April 2, 1916.

Photo by Ken Schlager

St. Ann’s Church
Three blocks north, the imposing St. Ann’s Church (704 Jefferson) is said to be the site of Sinatra’s first singing performance—at a church supper. Sinatra returned to the church in July 1984 for the annual St. Ann’s feast on a campaign stop for presidential candidate Ronald Reagan.

Photo by Ken Schlager

Dom’s Bakery
My next stop is Dom’s Bakery (506 Grand Street), which shipped boxes of crusty Italian peasant bread for Sinatra to a restaurant in California after the star had moved to the West Coast. “He liked everything burnt,” baker Dominic Castellitto tells me. “Everything had to be well done.”

Photo by Ken Schlager

Engine Co. No. 5
One block south of Dom’s is the nicely restored Engine Co. No. 5 firehouse (412 Grand Street), where Sinatra’s father, Marty Sinatra, served as captain. Today it’s a private residence.

Grace Scianalepore shows off the jukebox at Leo’s Grandevous. Guess whose songs are in heavy rotation? Photo by Ken Schlager

Leo’s Grandevous
I continue south on Grand to Second Street and step inside Leo’s Grandevous (200 Grand Street), a spacious Italian restaurant and bar owned by Nick DePalma, grandson of the original proprietor, Leo DiTerlizzi, and Leo’s wife, Tessie. On this day, DePalma’s sister, lifelong Hoboken resident Grace Scianalepore, is managing the bar. She explains that Leo’s was originally a pool hall. Leo and Tessie lived upstairs, where Tessie would prepare her Italian specialties as a treat for the pool-shooting patrons. Among the late-night clientele: the young Sinatra, just starting to make his name in Jersey clubs like the Rustic Tavern.

“My grandmother used to bring down mussels for the guys,” says Scianalepore. “Sinatra would drop in for a quick drink on his way home from a show.” DiTerlizzi became a huge Sinatra fan and, with his brothers, amassed a collection of Sinatra memorabilia that still blankets the restaurant’s walls.

Photo by Ken Schlager

Piccolo’s
Leaving Leo’s, I walk two blocks to Piccolo’s (92 Clinton Street), a pizza and cheesesteak joint and home to more Sinatra memorabilia. Here I encounter James Espinosa, a 55-year-old retired plumber, who eagerly relates his experience shining Sinatra’s shoes.  “Don’t dirty my socks,” Sinatra directed the young Espinosa. For a job well done, he gave Espinosa a $5 tip. Not bad for a quarter shine.

Photo by Ken Schlager

Demarest High School
From Piccolo’s, it’s a six-block walk to Demarest High School (Fourth and Garden streets). The massive building looms majestically over Church Square Park. But it must not have impressed the young Sinatra; accused of a prank, he was expelled after 47 days.

Lucille Burke dishes out treats and Sinatra stories at Lepore’s. Photo by Ken Schlager

Lepore’s Home Made Chocolates
Near the high school stands the new location of Lepore’s Home Made Chocolates (105 Fourth Street). In the 1980s, the superstar Sinatra would stop at the old location at Sixth and Garden when visiting his godfather to indulge in a favorite treat: chocolate-covered dried apricots. Mario Lepore, who founded the business 35 years ago, tells me Sinatra would send his limo driver into the shop to purchase the apricots by the trayful. “Whatever I had, he took.”

Behind the counter, Lucille Burke volunteers that she was born two doors down from Sinatra at 413 Monroe. Burke is too young to have encountered Sinatra, but she recalls stories of him singing on the street to anyone who would listen. “He’d grab anything—a stick, a twig—and sing into it like it was a microphone.”

Eager to share more stories, Burke opens her flip-phone and calls her older brother, Anthony Bencibenga, who lives in Virginia. I listen in as Bencibenga, 87, recalls the early days when Sinatra would return to Hoboken after gigs and visit his uncles’ restaurant on Jefferson Street, the original Balbo’s Pizzeria, for late-night plates of mussels and hot bread. “Everyone knew Frank loved mussels,” says Bencibenga.

Photo by Ken Schlager

703 Park Avenue
From Lepore’s, I head to Hoboken’s three remaining Sinatra family residences, each privately owned. Seen in succession, they testify to the family’s upward mobility as it moved step-by-step to the ritzier streets, ever closer to the Hudson River. My first stop is 703 Park Avenue, a narrow, five-story building with twin columns of copper-trimmed bay windows. The Sinatra family moved here in 1927, when Frank was 12.

Photo by Ken Schlager

841 Garden Street
In 1928, the Sinatra family moved to 841 Garden Street, one block closer to the water. This was Frank’s home throughout his teen years.

Photo by Ken Schlager

909 Hudson Street
Finally, three blocks closer to the waterfront, I gape up at 909 Hudson Street, an ornately appointed, five-story, red stone building that towers above its neighbors. After he made it big, Sinatra bought the single-family house for his parents. I stand back and imagine the debonair star escorting his glamorous second wife, Ava Gardner, up the steps of the impressive home for spaghetti dinners with her in-laws.

Frank Sinatra Memorial Park
I end the tour at Frank Sinatra Memorial Park, looking out on the river at Fourth Street and Frank Sinatra Drive. The city dedicated the park on July 14, 1998—the day the Sinatra family finally reached the waterfront.