How to Spend a Day in Hoboken

Ready to get a bit off the beaten path? While New York City never gets dull, there are amazing places to explore nearby that you might not have thought to visit! Here to share details of how to plan a perfect day in the town of Hoboken, New Jersey is local guide Iren.

How to Spend a Day in Hoboken

Have you ever heard of Hoboken, the charming town that lies right across the Hudson River from Manhattan? Most people know it because it's the birthplace of Ol' Blue Eyes, Frank Sinatra. But there is so much more to Mile Square City (yes, it's only slightly bigger than one square mile!) With its beautiful 19th-century architecture, fascinating history, excellent food, and spectacular views of New York City, Hoboken is a destination not to be missed.

Start with brunch

Start your Sunday with a brunch at Bin 14 (1314 Washington St), a restaurant owned by local celebrity chef Anthony Pino. Enjoy brunch staples or upscale Italian tapas (the chef's specialty!) as well as mouthwatering cocktails, all while listening to an excellent jazz trio featuring some of the NYC area's finest musicians. The place fills up fast, so reservations are strongly recommended!

Continue with a stroll along the waterfront

After your cocktails and eggs benedict, walk a few short blocks east until you reach the waterfront. You'll walk through the Shipyard—a fancy condo development bearing the name of its steamship building past. Behold the spectacular view of midtown, the Hudson Yards, and the Empire State Building right before your eyes!

Walk along the waterfront, and turn back into town to the corner of 11th Washington Streets—Hoboken's main artery. That's right—you are standing right where the first game of baseball was played on June 19, 1846. The area—an actual baseball field at the time—was a part of Elysian Fields, a glamorous 19th-century pleasure ground. The lovely Elysian Park, just one block south, bears its own claim to fame as the location for an important scene starring Marlon Brando in the classic movie On the Waterfront. The film—which won eight Oscars—was the first American film shot entirely on location . . . and all in Hoboken!

...And check out the beautiful brownstones on Hudson Street

As you walk south, take Hudson Street—one of the most picturesque streets in town—and fancy yourself back in the 19th century. Architecture lovers: take a look at the two Queen Anne houses at #921 and #923, both built in the 1890s. The whimsical, multitextured buildings might seem different, but if you look closely, they are exactly alike except for the domes.Further down, notice #909—when Frank Sinatra became a big star he bought this house for his parents, Marty and Dolly.The next couple of blocks are defined by the perfect rhythm and uniformity of adjacent houses lined up in rows right next to one another, forming a solid street facade. These are some of the finest examples of turn-of-the-century Italianate brownstones.

See the first engineering school in the country

After exploring Hudson Street, take 8th street towards the Hudson River, and you'll find yourself entering a college campus. You are now at Stevens—the first engineering school in the country (founded in 1870.) Feel free to meander, but make sure not to miss the Castle Point Observation Terrace. Located on the very bluff noticed by Henry Hudson in 1609, it opens up a magnificent vista with a sweeping view of Manhattan that stretches from the Verrazano Narrows to the George Washington Bridge. Do you see the cannon? Legend has it that this very cannon was used in the Revolutionary War against the British.

Moving in the same direction, make your way back down towards the waterfront. If you take the stairs down, look out for Sybil’s Cave. Though it appears rather dilapidated, the Gothic-style entrance (1832) used to lead to a mineral water spring enjoyed by visitors to the River Walk promenade, one of the country’s most frequented pleasure grounds. The place was the site of the still-unsolved murder of a beautiful cigar girl that inspired Edgar Allan Poe to write “The Mystery of Marie Rogêt”—the first modern detective story. An alternate way out of the campus will lead you to 6th Street. Walk one block south and you'll see another architectural delight—the Edwin A. Stevens Hall, designed in 1870 by Richard Upjohn, the architect that built Trinity Church on Wall Street.Head over to the waterfront for a visit to the "floating" Pier C Park. The odd-looking park is actually a historic footnote, being built as a tribute to the floating rowing and sailing clubhouses that lined the waterfront before trans-Atlantic shipping lines came to Hoboken in the 1860s. The original Pier C had a starring role in the film On the Waterfront, along with a small floating clubhouse that survived from an earlier era.

Time for a little snack break

At this point, you are probably tired and need a pick me up. Stop by Halifax (at W Hotel, 225 River St) for midday appetizers as well as fantastic views. Alternatively, you could step over to Washington Street and visit Carlo's Bakery (95 Washington St, from the hit show Cake Boss), where Buddy Valastro makes his whimsical culinary creations. Locals can go in without a line—visitors, on the other hand, have to wait in line patiently for a treat.

Stroll to the ferry terminal and pier

Now is the time to stop by the Hoboken Ferry Terminal. A landmark from the days when train stations were meant to be grand entrances to cities, the Lackawanna—a Beaux-Arts architecture masterpiece—fulfills that role to this day. Built in 1907, it combines elegance with practicality and recreates 16th-century Renaissance ideas using 20th-century materials (note the copper-adorned façade.) Built over water on a steel and concrete foundation, the double-decker ferry terminal was designed for passengers to arrive from the top deck while horses and carriages disembarked from the bottom. Take a peek inside the main waiting room to see an exquisite Tiffany glass ceiling.Right in front of the Ferry Terminal is another park called Pier A. The park offers breathtaking views of downtown Manhattan, especially at sunset. Though it looks idyllic now, the site was the spot of departure of the three million American troops en route to Europe to fight in WWI. Hoboken was the official port of embarkation, thus, the popular slogan, “Heaven, Hell, or Hoboken by Christmas.” President Woodrow Wilson sailed from here in 1918 to attend the Paris Peace Conference, where he proposed the formation of the League of Nations.

Dinner time

"YOU HAVEN'T BEEN TO HOBOKEN UNTIL YOU'VE EATEN AT LEOS." So why not dine in Leo Grandevous (200 Grand St, established in 1939)—the place where you can enjoy an authentic Italian meal while feeling the presence of Hoboken's own Frank Sinatra. On the way there, make sure to stop at a traditional Italian deli called Luca Brasi's (100 Park Ave). There are a few delis like this in town—with each proudly claiming to make the world's best mozzarella. I personally agree with them all. Luca Brasi's walls are adorned with Sinatra memorabilia, and they state "Food So Good It's Criminal."

Well, you be the judge . . .

Of course exploring Hoboken is even better with a local guide sharing stories along the way! You can book Iren’s History, Architecture and Taste of Hoboken Tour to make the most of your time here.