Times Square sometimes gets a bad reputation from tourists and locals alike. Sure, it can be crowded and many of the shops are selling overpriced tchotchkes that offer little in terms of true appreciation for the city. But in reality, Times Square is also a bona fide cultural landmark: a busy epicenter of all things entertainment and pop culture. It’s also been this way for over 100 years.
In the days of early New York, Times Square was known as “Long Acre” Square but became known as Times Square after 1905 when the New York Times moved their offices to the spacious intersection. The newspaper and the nearby Broadway shows helped turned Times Square into the brightly lit hub of activity and entertainment it is known today. And even though it has seen its ups and downs over the years—from a “dim-out” during WWII to save power to the notorious neighborhood decline of the 1970s—it has remained a New York landmark through and through.
Here are some of the best spots to check out around Times Square.
Best Place to Enjoy a Cocktail
If you want to duck into a cozy spot that takes you away from the lights and crowds but still gives your night some zing, look no further than The Rum House inside the Edison Hotel at 288 W. 47th Street. With a rich wood and leather interior, bouncy jazz music, and exceptionally well-crafted cocktails, this classic lounge is a great place to begin or end your Times Square night out.
Best Spot to Grab Some Good Coffee
If you’re looking to fuel up for the day, forget about your go-to coffee stops and head to the local coffee chain Gregorys Coffee located at 762 7th Avenue. Priding themselves on a higher quality brew than some well-known competitors, Gregorys has been caffeinating New Yorkers since 2006, but has really taken off in recent years—even earning a Forbes write-up. The 7th Avenue location puts you right in the heart of the Garment District, so you can sip your java alongside the stars of fashion luminaries like Marc Jacobs and Ralph Lauren.
Best Restaurant for a Fancy Steak Dinner
Sometimes when you’re in the heart of Manhattan you just want a perfectly cooked steak in an opulent setting with exceptional staff and ever-flowing drinks. To satisfy your extravagant desires, book a table at Hunt & Fish Club NYC at 125 W. 44th Street. The setting is ostentatious, the food is to die for, and the experience is one unique to New York.
Best Spot to See Good Comedy
There are plenty of comedy clubs in New York, but one that you can nearly always count on to deliver hilarious local and touring comics is Carolines at 1626 Broadway. In a part of town that is filled with people pushing different kinds of entertainment, Carolines is a sure bet for getting some laughs.
Best Live Music
New York is dotted with world-famous music venues, but one venue that can slip under the radar but consistently delivers great musicians in an intimate club setting is the Iridium. The focus at the Iridium is mostly rock, blues, and jazz, but the underground stage has hosted artists from across a wide range of musical genres.
Best Dive Bar
There’s no shortage of places to grab a drink in Times Square, but if you’re seeking out a unique New York bar experience look no further than Rudy’s Bar and Grill at 627 9th Avenue. As one of the first places to get a liquor license in the city after Prohibition ended in 1933, Rudy’s is a drinking institution just down the street from the glitz and noise of Times Square.
Best Sandwiches
It may be blasphemous to say, but one of the best sandwiches near Times Square is a Philly-style cheesesteak sandwich from Shorty’s. Located at 576 9th Avenue, this “enemy import” offers up authentic Philly cheesesteaks late into the night and, since it’s also a bar, you can also expect to have something on draft while watching an Eagles or Phillies game on one of the many TVs.
Best Spot to Soak It All In
While Times Square is a crowded mass of people, advertisements, traffic, and energy, there is an odd peace that comes along with sitting in the eye of the storm on the Red Steps in the middle of it all. Sitting atop a TKTS booth that sells same-day Broadway show tickets at healthy discounts, the Red Steps are a gleaming public piazza in the midst of the urban throngs. It’s nearly impossible to sit on these steps and not be at least a little impressed with the city symphony that will play out before you.
