Whether you’re a first-time visitor or a longtime local, everyone should witness the dazzling lights of Times Square at least once. Sure, the area is home to uninspired chain restaurants and tourist traps, but looking up at the larger-than-life billboards, neon signs, and towering buildings is sure to stoke your appetite for a bite of the Big Apple.
It makes sense that in an area known for theater performances, even the buildings are characters. Yes, even New York City’s ultra-modern Midtown offers historic sights for those who seek them. Architecture enthusiasts shouldn’t miss the neo-Georgian-style Music Box Theatre or Broadway’s oldest operating theater, the Lyceum Theater, built in 1903.
Music Box Theatre, 239 W 45th St, New York, NY, USA, +1 212 239 6200
Lyceum Theater, 149 W 45th St, New York, NY, USA, +1 212 239 6200
Enjoy a taste of history at The Knickerbocker Hotel
Visit Times Square’s Knickerbocker Hotel to imbibe at the birthplace of a beloved beverage. Legend has it that a bartender by the name of Martini di Arma di Taggia concocted an original cocktail here in 1912. The name of his creation? You guessed it: the martini. Rumor has it that New York great John D. Rockefeller popularized Martini’s eponymous drink, and the rest, as they say, is hooch history.
The Knickerbocker Hotel, 6 Times Square, New York, NY, USA, +1 212 204 4980
Catch the biggest names in comedy at Caroline’s
For those who think theater is all this area offers, we submit Caroline’s as a counterpoint. This legendary comedy club is known for hosting industry greats, such as Chris Rock, Kevin Nealon, and Tracy Morgan. Of course, being a Broadway theater, Caroline’s is superior to your average comedy club, even winning a National Honor Award for Interiors upon its opening.
Caroline’s, 1626 Broadway, New York, NY, USA, +1 212 757 4100
There’s a reason this ‘hood is nicknamed Manhattan’s Theatre District. Or, rather, 39 reasons. This area, which packs a whopping 39 theaters into a 14-block (and three-avenue) city stretch, boasts the world’s highest concentration of performance venues. Whether you’re coveting a chair at a classic Broadway show or a contemporary smash, the Theatre District is your ideal destination.
Dine on Restaurant Row
Foodies flock to the Theatre District’s Restaurant Row to eat their way around the world without leaving the city. The area, which entails West 46th Street between Eighth and Ninth Avenues, was officially designated in 1973 when 16 eateries called the stretch home. Today, the block’s bounty has more than doubled and includes everything from Brazilian to Japanese to Thai cuisine.
Visit a site of television history at the Ed Sullivan Theater
Built in the 1920s, the Ed Sullivan Theater has lived many lives. The historic site of The Ed Sullivan Show, The Beatles’ debut U.S. performance, and David Letterman’s 22-year-long Late Show is now home to the popular The Late Show with Stephen Colbert. With credits like those, it’s no wonder that this theater landed a spot on the National Register of Historic Places as well as New York City landmark status.
We wouldn’t ordinarily advise exploring New York City alleys, but we have to make an exception for this historic destination. Schubert Alley is widely considered to be the heart of Manhattan’s Theatre District (literally, the narrow stretch marks the area’s geographical center), and for good reason: this 300-foot-long (91.4 meters) alley is the best site for spotting Broadway’s biggest names as they dash between theaters.
Radio City Music Hall
From stand-up shows to singing to seasonal fun, this New York City stage hosts it all. Get your entertainment fix at Radio City Music Hall, credited as being the “largest indoor theatre in the world.” In fact, the only thing bigger than the theater itself is the talent that graces its stage. Dave Chappelle, Tony Bennett, and The New York City Rockettes accompanied by Santa Claus himself have all brought their gifts (literally, in some cases) to this iconic venue.
Radio City Music Hall, 1260 6th Ave, New York, NY, USA, +1 212 465 6741
Explore off-broadway shows
For an insider’s spin on New York City theater, check out one of the area’s many off-broadway shows. In the interest of helping you avoid any painful theater experiences, we recommend heading straight to Astor Place Theatre or New World Stages, both of which are known for their great programming.
Astor Place Theatre, 434 Lafayette St, New York, NY, USA, +1 212 254 4371
New World Stages, 340 W 50th St, New York, NY, USA, +1 646 871 1730
Indulge in some of the city’s best Italian cuisine
Say “see you later” to Little Italy: Manhattan’s Theatre District is the city’s true hub for Italian cuisine. From upscale eats to down-home dining, this neighborhood will quench your craving for Italian. Tuck into authentic pasta, pizza, and all the vino you can drink at Carmine’s, Becco, and Trattoria Trecolori.
In a historic area such as this, newcomer attractions are always exciting. The larger-than-life Gulliver’s Gate (the establishment measures a full city-block wide) specializes in miniature amusement. Here, a 50,000-square-foot (4,645-square-meter) exhibition spanning four rooms will satisfy your wanderlust with small-scale models of Asia, Africa, Europe, and the Americas.
Gulliver’s Gate, 216 W 44th St, New York, NY, USA, +1 212 235 2016
This local legend baring his soul (and a few other things)
Shield your eyes (or take out your camera) when New York’s famous Naked Cowboy appears. A local street performer whose—er, unique—routine has earned him international recognition, the Naked Cowboy has been captivating Times Square audiences for years. No need to be too alarmed, though: this local act is more OMG than NSFW.