What to Do in Hoboken—Sinatra, Baseball, Hamilton, and New York's Best View

Once you’ve left the Big Apple’s behind, you shouldn’t forget about New York just yet. All along Hoboken's Hudson River Waterfront Walkway, visitors can take in great views of the NYC skyline that you just can’t get when you’re standing in the middle of it. At the walkway’s start you’ll find Pier A Park, a lovely green space encircled by a promenade. Continue your stroll and soon after, you’ll hit Pier C Park, a unique playground that extends over the water. Walk even further uptown to reach Pier 13, which comes to life in the spring and summer months with food trucks and watery activities such as kayaking, paddleboarding, and jet skiing.

 

Because Hoboken is only one square mile, everything is within walking distance—and Washington Street is at the center of it all. The extra-wide main street is a melting pot of old and new, with mom-and-pop shops that have been around for over 50 years next to popular chain stores open only for a few months. This makes Hoboken feel like a homey small town and a modern city at the same time. Browse used books at Symposia Bookstore (510 Washington St.) or take advantage of the outdoor seating at one of the excellent restaurants, such as Cuban eatery La Isla (104 Washington St.), which was featured on Food Network’s Throwdown with Bobby Flay. 

 

Made famous by TLC’s Cake Boss, Carlo’s Bakery (95 Washington St.) now has over 20 locations, but Hoboken has the original. The bakery has been a mainstay on Washington Street since 1910. Skip the cake or cookies and instead taste a signature Italian pastry, like a cannoli or “lobster tail” stuffed with cream. If you’re lucky, you might even spot owner Buddy Valastro or another member of his family; there’s no scheduled day when the Cake Boss stars are in, but they do stop by from time to time. For a hands-on experience, sign up for a cake decorating class at Carlo’s Bakery Factory (631 Grove St.) in nearby Jersey City, just a 15-minute walk away. 

 

When Germany became the enemy in World War I, the demographics in “Little Bremen,” as Hoboken was then known for its large German population, shifted dramatically. Amid an atmosphere of xenophobia, German dock workers were fired and many were interned on Ellis Island. Italian families moved in to take their places, bringing their penchant for creating delicious dishes with them. Today, pizzerias can be found on almost every block. If bigger is better, then long-time favorite Benny Tudino’s (622 Washington St.) is the place to go—the slice of pizza you’ll receive here can only be described as humongous. For quality over quantity, visit Napoli’s (1118 Washington St.) a few blocks up on 11th Street, featuring traditional toppings done right (as well as abundant gluten-free options). For a more upscale experience, try Panello (720 Monroe St.), known not only for gourmet pizzas but also for pastas, entrees, and salads. We recommend the Diabolo Dolce, a white pie with fresh mozzarella, Calabrian chiles, olives, kale, and drizzled honey.

 

Hoboken’s Elysian Fields was the site of the first officially recorded organized baseball game. On June 19th, 1846, the New York Base Ball Club beat the Knickerbockers on this historic spot. Although the field no longer exists, a bronze plaque stands at 11th and Washington Street to mark the location. The positions of all the bases are shown around the plaque with their respective numbers set into the sidewalk in brass. An “H” marks home plate.

The city’s most famous hometown hero would have to be Frank Sinatra. Head to 415 Monroe Street and you’ll find a star on the sidewalk outside the apartment building where Ol’ Blue Eyes lived as a child. The Hoboken Historical Museum (1301 Hudson St.) celebrated the crooner’s centennial in 2015 with an exhibit featuring photographs, artifacts, music, and interactive displays. You can learn all about Hoboken’s rich history via the museum’s frequently rotating exhibits, which have focused on the city’s culinary traditions, the Hudson River, immigration, and much more. 

Though not technically in Hoboken, the Weehawken Dueling Grounds are only about a half-hour walk or 10-minute drive away. The infamous duel between Alexander Hamilton and Aaron Burr that left the 10-dollar Founding Father mortally wounded took place here—as did many other face-offs featuring lesser known opponents. A bust of Hamilton can be found at the site next to a small boulder, the very rock he was thought to have rested on after being injured. To reach the dueling grounds, leave Hoboken on Park Avenue, bearing right to Kennedy Boulevard East.

 

Say goodbye to Broadway prices—without sacrificing quality—at Mile Square Theatre at 14th and Clinton Street. This nonprofit professional theater produces a wide variety of classic and contemporary plays and musicals year-round, including a number of kid-friendly shows. The troupe also puts up 7th Inning Stretch, an annual festival of baseball-themed plays in celebration of Hoboken’s pivotal role in the history of the national pastime. 

 

Considering that Hoboken has the most liquor licenses per square mile in all of the United States, it’s no wonder nightlife is vibrant here. Sports bars with dance floors dominate the scene downtown; some of these spots lie along the waterfront, so you can marvel at city views amid the revelry. For an excellent glass of wine, go to Bin 14 (1314 Washington St.) and choose from a list with more than 75 options. Beer lovers won’t want to miss the authentic Austro-Hungarian Pilsener Haus & Biergarten (1422 Grand St.). Despite its somewhat remote location, more than 50 American and European bottled craft beers and more than 20 imported drafts make it well worth the trek. There are sausages, schnitzels, and strudels to complement the drinks. Antique Bar and Bakery at 1st and Willow Street is the place for cocktails—and a nightcap on weekends, when it stays open until 3am.

 

To get to Hoboken, take a Port Authority bus or hop on the PATH train, which you can ride with a swipe from the same MetroCard you use in NYC. The PATH system is sort of like the subway, but cleaner and with fewer stations, and if you take it, you’ll be let off right next to the historic Lackawanna Rail Terminal. The ferry, which you can catch at W. 39th Street, Pier 11, or Brookfield Place, is another fast, scenic option. It’s especially nice to sit on the boat’s open upper level in warm weather.