Choosing an old-school restaurant, café, or bar that’s steeped in history is an easy way to make your Valentine’s Day date special. All of the mom-and-pop businesses we will be highlighting have stood the test of time in a city known for its rapid pace of change. We have included pairings for dinner and drinks/dessert in Manhattan, Brooklyn, the Bronx, and Queens. Whether it be a romantic ambiance, delicious specialities, the glow of neon that washes over their facade, hand-painted murals along their interior walls, or a pleasant mix of all of these things, these choices will help make the night a success. — James and Karla Murray

We start off in the East Village with two vintage locations set on quiet side streets.

JOHN’S of 12th STREET at #302 near Second Avenue has been in business since 1908. It is one of the oldest Italian restaurants in the East Village and has its original Belgian mosaic tile floor, walls inlaid with terrazzo, and oil murals painted on canvas depicting scenes of the city-states of Italy. We highly recommend checking out the back room to see the giant tower of thousands of candles burning.

Nick Sitnycky, owner of John’s Italian Restaurant, shared, “This restaurant has an interesting history in that it operated as a speakeasy during Prohibition. John ran the restaurant on the ground floor while his wife was the brew master and served her homemade hooch out of espresso cups. The tradition of burning candles in the back room started as a celebration of the end of Prohibition. The candles have been burning back there since 1938 and the collection just keeps growing. Although we have been a traditional Italian restaurant for over 107 years and have kept the original menu, we have also added our own off-menu specials and introduced a vegan menu with a vegan take on traditional Italian foods. This is the first time in a tablecloth restaurant that there is both a regular and vegan menu, which closely mirrors the traditional menu.”

After the warmth of John’s it’s a short walk to Veniero Pasticceria, located on 11th Street near First Avenue for dessert.

VENIERO PASTICCERIA and CAFFE was established in 1894 by Antonio Veniero and is the only family-run Italian pasticceria left in the East Village, which once had a huge Italian population. It retains much of its original interior, including the hand-stamped metal ceiling, terrazzo floors, and wood display cases and mirrors. Gracing the façade is a huge overhanging neon sign from the 1940s. Robert Zerilli told us, “I am the fourth generation owner. A lot has changed here over the years, including the pastries and cakes we offer. We still serve many of the true Italian specialties such as our cheesecakes, biscotti (Italian biscuits) and Italian butter cookies, but we have also expanded the offerings instead of just profiting from the same old thing over and over again. We bake so many cakes and pastries that we go through about 1,000 pounds of sugar every week.”

Tourist-heavy MacDougal Street in Greenwich Village has two treasures that hide in plain sight on the busy blocks south of Washington Square Park.

MONTE’S TRATTORIA is a romantic Italian restaurant at 97 MacDougal Street between Minetta Lane and Bleecker Street, which has been in business since 1918. It has been owned by chef Pietro Mosconi and his family since 1983 and continues to serve authentic Northern Italian dishes. Pietro Mosconi told us, “In 1976, my sister and I opened up the restaurant, Villa Mosconi, down the block from Monte’s. In 1983, I had the opportunity to purchase Monte’s from the original owner. I installed a new kitchen and dining room and even put in a private room upstairs for parties or for a la carte dining when we are busy. What is original is the neon sign outside, which was installed in the 1950s. I kept the signage because I liked it and also felt strongly about keeping the name Monte’s, which was shortened from Monteverde, a city in Italy known as the ‘green mountain.'”

After dining at Monte’s Trattoria take a walk down MacDougal Street’s narrow sidewalks to Caffé Reggio, the first caffé in the United States to serve cappuccino.  A variety of coffee, teas and desserts are served in a beautiful setting with authentic Italian Renaissance artwork gracing the walls, including paintings from the school of Caravaggio.

CAFFÉ REGGIO, located on MacDougal Street between W. 3rd Street and Minetta Lane, has been open since 1927. The caffé is famous for its vintage espresso machine, which was imported from Italy by the original owner, Domenico Parisi.  Mr. Parisi spent his life savings of $1,000 to import the chrome and bronze espresso machine to his café.  The machine was made in 1902 and was the first of its kind; it features a base formed by dragons and an angel sitting on its top.  When filled with hot water, the machine makes a cup of espresso in about three seconds.

Manhattan’s West Village and Meat Packing District have both experienced monumental changes and continue to feel a full-on gentrification assault, but it’s still possible to have a romantic old school evening.  Old Homestead, New York City’s oldest steakhouse, is just north of 14th street on 56 Ninth Avenue.

OLD HOMESTEAD STEAKHOUSE is one of the longest continually operating restaurants in the United States. It was founded in 1868 and has been run by the same family for three generations since 1951.

Steve Mangione, head of PR for Old Homestead Restaurant explained, “This restaurant has always specialized in what it considers the most important major food groups: beef, beef, beef and beef. It is known for its prime aged USDA Texas-size slabs of beef, including its signature sirloin, porterhouse, prime rib and filet mignon. For the non-meat eaters, Old Homestead also offers whale-size lobsters and seafood towers filled with gargantuan shrimp and colossal crab. Since it opened its doors in 1868, Old Homestead attracted both locals and visitors who could afford to venture “all the way up to 14th Street” and splurge on an entire meal of sirloin steak with salad and sides for 8 cents. Now the same meal costs $50 dollars for the steak alone, with salad and sides costing extra.”

After dinner at Old Homestead, bundle up for a romantic stroll down tree-lined Hudson Street to another historic locale, this time for drinks at The White Horse Tavern. Once home to longshoremen on their “lunch” breaks from the nearby docks that once lined the river, it is now home to a diverse crowd.

WHITE HORSE TAVERN on Hudson Street at 11th Street has been in business since 1880. It is one of the few wood-frame structures still in existence in New York City and has an original interior including a tin ceiling, wooden bar and horse-head lamp fixtures. The overhanging neon sign made of cobalt blue enamel was installed in the 1940s. Eddie Brennan, who has owned the tavern since 1967, told us, “During Prohibition it was business as usual here at the tavern. Jimmy Walker, who was Mayor at the time, was born down the street on Leroy and went to school at St. Veronica’s where my father went to school and where I also went to school. So when Prohibition hit, nobody closed the tavern. It was that simple. This was the last place Dylan Thomas had drinks at before he became ill and died in 1953.”

Down in Chinatown, authentic Dim Sum can still be found at our favorite Nom Wah Tea Parlor located on narrow and crooked Doyers Street, once called The Bloody Angle.

NOM WAH TEA PARLOR on 13 Doyers Street is the oldest dim sum restaurant in Chinatown. It was founded in 1920 and is now being run by second generation owner Wilson Tang. Its gorgeous vintage sign was installed around 1968. Most of the interior is original, including the lunch counter and stools. Wilson Tang revealed to us, “As far as Chinese restaurants are concerned, I am able to bridge the gap between a traditional Chinese place and an American-Chinese place. I am probably one of the few Chinese people in New York who has stuck with the family business and also brought it to the next level. This restaurant was originally more of a bakery and tea parlor but my whole idea when taking it over, was to serve dim sum all day long. We are probably one of the few places that serve dim sum almost exclusively all day long.”

After dinner at Nom Wah, take a short walk to 195 Grand Street near Mulberry, to visit one of the last vestiges of what remains of Little Italy as Chinatown continues to spread north of Canal Street.

FERRARA BAKERY & CAFÉ was established in 1892 by Italian immigrants Antonio Ferrara and Enrico Scope. Ferrara’s is considered America’s first espresso bar. The café later added Italian specialties including cannoli, sfogliatella, and gelati to its menu. Ferrara’s is currently owned by the fifth generation of the Lepore family. In addition to their on-site bakery and two-floor café, they ship throughout the continental United States. The serve a full line of coffees, pastries, specialty cakes, wedding cakes, ice cream and gelati.

Further uptown in Manhattan is Rolf’s German Restaurant. which is especially famous for the over-the-top interior Christmas decorations.

ROLF’S GERMAN RESTAURANT located at 231 Third Avenue at 22nd Street has been in business since 1968. It is known for its traditional German dishes like Weiner Schnitzel, Bratwurst, Knackwurst and Weisswurst. Bob Maisano, explained that, “The original owner was Rolf Hoffman and I took the business over from him in 1981 and have kept the menu the same. Our customers really appreciate the consistency of our dishes as well as their authenticity. We have many Germans who tell us that our food tastes just like it does back home, and to us, that is the biggest compliment.”

After a hearty dinner at Rolf’s, stroll past Gramercy’s famous private park and along historic townhouse lined streets to the Old Town Bar for drinks.

OLD TOWN BAR at 45 East 18th Street near Park Avenue South was founded in 1892.  It has been in the same family since the early 1980s, and is now being run by the second-generation family member, Gerard Meagher. Gerard told us,“The entire interior is pretty much original. We have a mahogany bar with a marble top, which at 55 feet long, is one of the longest mahogany bars in New York. We have 258 square feet of bevel-edged plate mirrors and original gas-lit lamps, which were rewired once electricity became available. We also have our original 16-foot tin ceilings and have giant shoulder-height porcelain urinals in the men’s’ bathroom that were made by Hinsdale in 1910.”

Over in Brooklyn, set your sights for Queen Ristorante in Cobble Hill, with its glowing vintage neon sign.

QUEEN RISTORANTE on 84 Court near Livingston Street is a second-generation family-owned Italian restaurant, which was founded in 1958. It has been in its present location since 1989. Vincent Vitiello, second-generation co-owner, told us, “We still have some items on the menu that were from my father’s original Italian recipes, but we have changed and updated things quite a bit. Even though there is a neighborhood feel to our restaurant, we try to keep the food at a world-class level but with a neighborhood sensibility. The fact that we have been in business over 50 years with consistently high ratings from the critics attests to the fact that we are one of the best Italian restaurants in Brooklyn and the top in all of New York City.”

After your red-sauce dinner at Queen, take a walk down Court Street; turn right on Atlantic Avenue and head to the historic Montero Bar & Grill for drinks. Another great vintage neon sign guides the way to 73 Atlantic Avenue near Hicks Street.

MONTERO BAR & GRILL was founded in 1939 and is one of the last old longshoreman’s bars on Atlantic Avenue. It is decorated with nautical memorabilia and has a vintage cash register and pool table. Go now, because its future is uncertain, as the building it’s located in (along with six neighboring buildings) is for sale for $65 million.

Tucked away on a quiet street in the Columbia Street Waterfront District, you’ll find another romantic old school Italian restaurant, Fernandino’s Focacceria.

FERDINANDO’S FOCACCERIA, located on 151 Union Street by Columbia Street, has been in business since 1904. It has a vintage décor and specializes in classic Sicilian food including homemade rice balls, focaccia, and panelle. Francesco Buffa, the second-generation owner, told us, “I began working here in 1972 for Ferdinando, who taught me everything from A to Z about this place. In 1975, I got engaged to his daughter Antoinette but six months later my father-in-law passed away. It was a very hard time because of our loss and also because the neighborhood was changing drastically. The longshoremen were leaving and many Italians were moving out of the area. I decided to concentrate on lunch and dinner but still served focaccia, which is basically a hot sandwich made with bread that is a round shape and filled with things such as cheese and calf’s spleen. The reason why the restaurant has been such a success over the years is because of my father-in-laws recipes and his old Sicilian standards of quality and tradition.”

After dinner at Ferdinando’s, take a short taxi ride down Van Brunt Street to Sunny’s Bar in Red Hook.

SUNNY’S BAR at 253 Conover Street has been owned and operated by the Balzano family since the late 1800s. After being flooded by Super Storm Sandy in 2012, the community banded together to repair and restore the beloved bar. Tone Johansen, co-owner, told us, “This bar has a long nautical history as it catered to all the seamen who lived and worked around the neighborhood. The mainstay of our business now is no longer seamen, because we have attracted a lot of young, new customers to our bar, who have found it after walking around the waterfront area or shopping at nearby IKEA.”

City Island in the Bronx is romantic in a Cape Cod kind of way any time of year. Take a trip over the narrow metal bridge from the Bronx mainland to an island with a small fishing village vibe. City Island is chock full of seafood restaurants, but we chose to highlight The Original Crab Shanty.

THE ORIGINAL CRAB SHANTY RESTAURANT located at 361 City Island Avenue was founded in 1977 and serves both seafood and Italian style dishes. In the early 1900s, the building it’s in functioned as a silent movie theater, complete with tall ceilings. The Original Crab Shanty, although not located on the water like many of its nearby competitors, became very popular due to its large portions of great quality food, reasonable prices and great service.

Many of the same waitresses and staff have been working at The Original Crab Shanty since it opened. Michelle Valenti-Debitetto told us, “We are definitely one of the oldest continuously run family restaurants in City Island. I’ve been the manager for the last 20 years but I started working here when I was only twelve years old as a salad girl. We make people feel comfortable and welcome them into our restaurant as if they were dining in their own home.”

After dinner, head back to the mainland for dessert and espresso in Belmont, or the “Little Italy of The Bronx.” Egidio Pastry’s white neon signage marks the corner as the spot for authentic Italian pastries.

EGIDIO’S PASTRY SHOP, located on the corner of East 187th Street at Hughes Avenue, was founded in 1912 by Pasquale Egidio. They specialize in Italian pastries including strufolle, biscotti, cannoli and sfogliatelle. Carmela Lucciola, who has owned the shop since 1987, told us, “Many of our customers have been coming here for years and respect that I have kept the menu the same and treat people with the same welcoming attitude as the Egidio family always did. On the weekends, which are our busiest time of the week, we often get three generations of family members stopping by for pastries. The neon sign we have outside is original and was installed in the 1960s. Even though it is difficult to maintain, I always try to keep it lit because to me it is an important symbol of the store.”

Instead of dinner and dessert in Queens, we decided to suggest a movie at an independent theater in Forest Hills followed by dessert. CINEMART CINEMAS at 106-03 Metropolitan Avenue at 72nd Road features first-run & art house films. The theater has an adjacent, cozy cafe but we recommend to head directly across 72nd Road to the absolute jewel, Eddie’s Sweet Shop.

EDDIE’S SWEET SHOP on Metropolitan Avenue has been in business for nearly a century.  It is known for its delicious homemade ice cream in over 18 flavors. Its neon signage is from 1968 but the interior including the marble counters, stained glass windows, tin ceiling and inlaid wood cabinetry is original. (visible in the photo above) Vito Citrano, the present owner told us that he “first worked as a counter boy for Eddie and then took over the store when he retired but didn’t change a thing.”

Courtesy of: Gothamist.com