It’s not uncommon to see an empty weekend as a daunting thing — especially when living in an area full of countless fun things to do. Hoboken may only be one square mile, but it is filled with great food, culture, history, and community, making it impossible to actually see everything in just 36 hours. Because of this, we have curated a thoughtfully laid out weekend plan that can be followed hour by hour, or just be used as inspiration for your weekend plans. This list is not intended to quickly cross famous Hoboken “landmarks” off your list of things to do and see or highlight specific events happening on specific weekends — instead, this list will create an efficient and enjoyable 36-hour experience in the Mile Square, through a specific lens, that can be used at any time.
This month, music will lead us through 36 hours in Hoboken. Read on for a full weekend itinerary, including live piano duels, Frank Sinatra’s old home, and sandwiches inspired by iconic musicians.
Friday
5:30PM: Get Dinner at Leo’s Grandevous | 200 Grand Street
(Photo credit: @leosgrandevous)
Leo’s is known for being one of the oldest restaurants in Hoboken, serving top-notch traditional Italian cuisine. It is also known for being one of Frank Sinatra’s favorite local spots back from his time in Hoboken. In fact, the restaurant still reserves a chair for him and honors his legacy with photos and memorabilia covering the walls.
Read More: The ULTIMATE Hoboken Bucket List — A Guide to the Mile Square’s Gems
8PM: Grab a Drink + Hear Live Music at Finnegan’s Pub | 734 Willow Avenue
Walk just a few blocks up and Finnegan’s will welcome you in as family. They have live music from great local musicians every Friday and Saturday night. Grab a beer, enjoy the music that fills the room, and watch your favorite teams playing up on their big screen TVs or challenge your friends to a game of darts.
11PM: Travel Back to the ’90s With a Live Rock Band at Willie McBride’s | 616 Grand Street
Head back to Grand Street for a throwback night full of live alternative and punk rock music. Dance the night away while singing along to Nirvana, The Killers, Bruce Springsteen, Fall Out Boy, Jimmy Eat World, and so much more. Every weekend brings in a new local cover band that is sure to party like it’s 1999.
Total: 7 hours
Saturday
11AM: Take a Dance Class — Regardless of Your Experience
Try something new — or bring back your old hobby — and take an adult dance class in Hoboken. The Mile Square Theatre, The Studio, Hoboken Latin + Ballroom, and Jane DO all offer dance classes for different levels of experience. Never taken a dance class in your life? No problem! The Studio has classes for beginners that will get you started on a beautiful dancing journey. If a formal dance class isn’t for you, check out a Dance Cardio class at Crunch Fitness, Jane Do, or Impact Fitness.
12:30PM: Shop for Some Music at Tunes | 225 Washington Street
After burning up a sweat to upbeat music, relax by getting lost in the stacks of vinyl records, CDs, and even cassette tapes at Tunes — Hoboken’s one and only music shop. Open since 1995, this record store has been a Hoboken staple for almost 30 years. Chip Heuisler, owner of Tunes, is often on-site and happy to help customers find what they are looking for, whether it’s a just-released album or a vintage record from the ‘70s.
2PM: Take in the City Skyline + Get Lunch at Blue Eyes | 525 Sinatra Drive
When spending a music-filled weekend in Hoboken, this stop is simply a must. Blue Eyes is one of the only true waterfront restaurants in Hoboken, giving it the ultimate skyline view for patrons. Their brick oven is made out of bricks flown in from Naples, Italy, providing that authentic Italian taste for their homemade pizzas. HG pro tip: keep an eye out for the karaoke nights.
3PM: Sit in Sinatra Park
Walk out of Blue Eyes and find a spot on the grass or take a waterfront-facing bench and enjoy the views. On a nice sunny day, this is prime people-watching territory, and a great place to just enjoy the beauty that Hoboken is known for. This is also a great spot to grab those Insta-worthy photos of the skyline. The park is between 4th and 5th Street on Sinatra Drive.
6PM: Dine at Barbès | 1300 Park Avenue
Take a walk uptown and a bit west to Barbes, which has a menu that “takes lead from Morocco, with traditional French brasserie fare”. They offer live music from Thursday through Saturday, and it is always an interesting mix of local musicians. If choosing to visit earlier in the day, they also have a killer drag brunch on Sundays. Check their Instagram for current events.
8PM: Watch Pianists Duel at House of ‘Que | 333 River Street
The perfect event for any music lover, Dueling Pianos takes place on weekends at both House of ‘Que and the Madd Hatter on Washington Street. Watch in awe as two talented pianists turn out countless songs on their respective pianos, at the request of the audience. Participants vote for songs with their dollars at this live music event, and whichever song gets the most funds is played by the performers. But don’t get too excited — songs can be outbid by the audience and cut off mid-song. Dueling Pianos is endless fun and the audience always really gets into the performances.
11PM: Grab a Nightcap at Backstage at Sirenetta | 1039 Washington Street
(Photo credit: @backstagehoboken)
Drink like a VIP and end an exciting Saturday at Sirenetta’s Backstage — an upscale cocktail lounge at the back of Sirenetta’s restaurant. The lounge pays homage to the old Maxwell’s Tavern that used to sit in the same space, which was known for showcasing some of the top bands of the time.
Total: 13 hours
Sunday
10AM: Take a Music-Filled Yoga Class at Urban Souls | 100 Hudson Street
This is not your mom’s yoga class. The Urban Warriors class offered at Urban Souls is a yoga class that breathes to the rhythm of a DJ-quality playlist, sometimes even offering a theme. The poses will start to feel like a dance routine as the music and energy fill the room, and the sweat will come easily.
11:30AM: Take a Frank Sinatra Walking Tour
Walk all throughout Hoboken and see the sights that Sinatra himself laid eyes on while he lived and visited here. The tour will take you past his old apartment, the house he bought for his parents, the statue raised in his honor on the waterfront, the restaurants he frequented, and more.
1:30PM: Grab a Sandwich from Vito’s Deli | 806 Washington Street
(Photo credit: @vitosdelihoboken)
Swing by one of Hoboken’s best Italian delis, Vito’s, and order a Sinatra Hero. The specialty sandwich includes soppressata, salami, mutz, sun-dried tomatoes, and a choice of spread. Or try the Sophia Loren — a famous actress who also recorded over two dozen songs throughout her career. This sandwich has mortadella, imported Cappi, mutz, artichokes, and pesto. If Lisa’s Deli is more convenient — located at 901 Park Avenue — they also offer a Sinatra Special hero or wrap.
See More: Where to Take Your Parents Out to Eat in North Jersey
2:30PM: Learn Some Hoboken Musical History at the Hoboken Historical Museum | 1301 Hudson Street
The Hoboken Historical Museum has a Frank Sinatra corner with all the history of his life here in Hoboken. The museum is open from 2PM-5PM on weekends.
Please note: This article was inspired by the New York Times series titled 36 Hours.
