In New York’s Lower East Side, trendy penthouses in glass skyscrapers now dot the skyline, but a rich, grimy character lives underneath. Even with rapid development, the neighborhood hasn’t totally lost touch with its long history of being a diverse cultural hub. At the turn of the 20th Century, the LES was the most densely populated place in the world. Jews, Irish, Italians, Poles and Ukrainians populated the neighborhood and sold goods out of pushcarts through the streets. Hispanic immigrants joined them, congregating east of Avenue A. Before Brooklyn was a thing, Downtown was the home of artists and other ex-pats escaping more moneyed Manhattanites. And despite a thriving late-20th Century culture that produced the Beats, Punk and New Wave, it wasn’t so long ago that respectable types wouldn’t venture round these parts. After all, the protagonist in Bright Lights, Big City lamented that a fellow young party goer wouldn’t accompany him “below Fourteenth Street because, he said, he didn’t have a lowlife visa.”
Eventually though, the money started to congregate south of 14th Street. Kids of affluent New Yorkers, such as Lady Gaga and the members of The Strokes, launched their careers there. And others followed to patronize great shops, bars and restaurants. Sure, during the past few decades, the LES’s ethnically and culturally distinct enclaves have been chiseled away to form new neighborhoods, including Chinatown to the south and the East Village to the north. And in the last few years, rents have driven the hip kids over into Brooklyn. The neighborhood is now less the home of young artists and more the stomping grounds of Ross from Friends and Padma from Top Chef. But you could still spend a lifetime of nights going out in Manhattan’s vibrant downtown. Here’s how to spend one of them.
3:06 P.M. Unload your field bags at the Bowery Hotel a boutique brick tower in the heart of the East Village. The charming hotel—with its leather chairs, Oriental rugs and potted palms—looks like a Rudyard Kipling wet dream. Every room comes with impressive floor-to-ceiling factory windows, so splurge on a bed on an upper floor for the best views. After soaking in your panoramic sights of Manhattan, head to the nearby Tenement Museum to experience the not-as-glamorous life of 19th Century immigrants. The museum is housed in a five-story, brick tenement building from 1863. Over the course of 70 years, an estimated 7,000 working-class transplants from 20 different countries lived in the two-dozen apartments inside. The museum has restored six of these humble homes in historically accurate fashion.
5:17 P.M. Stroll Rivington, Stanton, and Houston streets to get a feel for how the Lower East Side has changed over the years. Primitive, but mostly remodeled, tenement buildings stand alongside chic bars, restaurants and shops. Pick up some old-timey bulk sweets like Atomic Fireballs and Big League Chew at the colorful Economy Candy. Browse the cock ring vibrators at the hip, adult-toy shop Babeland. Then snack at Prohibition Bakery, the only cupcake shop in the world that’s 21+. The boozy bakery makes mini confections that imitate the taste—and alcohol content—of your favorite cocktails. You will actually get buzzed after a few of these. We recommend the Old Fashioned (orange cake with whiskey, bitters and a whiskey-soaked cherry), Car Bomb (chocolate cake with whiskey, Bailey’s and stout), and the Scotch & Cigar, a molasses cupcake made with Laphroaig and smoky tobacco. But stay away from the unpleasant Margarita; there’s a reason why you don’t hear about people baking with tequila.
6:45 P.M. Sip a few pre-dinner drinks at Pouring Ribbons, an inventive cocktail bar from the guys behind the mega-popular Death + Company. At Pouring Ribbons, the menu helps decipher alien ingredients by rating the bar’s mixed drinks on a matrix scale of Refreshing to Spirituous and Comforting to Adventurous. For example, the “Sedgwick Avenue” (La Favorite Ambre rum, Cocchi Vermouth Di Torino, Tanqueray gin, orange marmalade and BBQ bitters) is a hell of a lot more Spirituous and Adventurous than the Refreshing and Comforting “Zwack Morris” (Messmer Pinot Noir, orange, Zwack, cinnamon syrup and Unicum Plum). Try a flight of Chartreuse for a rare sampling of ancient spirits made by Carthusian monks.
8:31 P.M. Okay, okay, Pearl & Ash is on the wrong side of the Bowery to be the LES, but all these micro-neighborhoods are just a fiction created by real estate agents anyway. Besides, this year-old restaurant is worth schlepping across the street for. Chef Richard Kuo spent time at molecular gastronomy pioneer Wylie DuFresne’s wd-50, but pulls back on deploying all of Wylie’s space-age techniques. Order a bunch of plates to share, starting with the a couple servings of the bread with chicken butter, a whipped confection of rendered chicken fat, butter and maple syrup. Cardiac arrest never tasted so good. Get the potatoes with chorizo, the pork meatballs and the lamb belly—it’s like Little Bo Peep meets bacon. And you’ve got to try Kuo’s signature dish, the fried octopus. He marinates the tentacles in a Japanese spice blend for 12 hours, then cooks them sous vides for 24 hours and fries them to order. What to drink? That’s not for you to decide. Put yourself in the capable hands of wine director Patrick Cappiello, whose expertise, enthusiasm, and vast, yet affordable, list made The New York Times dub Pearl & Ash New York City’s “most exciting place to drink wine.”
10:34 P.M. Amy Poehler’s iconic comedy school in Chelsea, the Upright Citizens Brigade, has a little brother in the East Village. Pop into UCB East any night during the week for stand-up, sketch, and improv shows starring both up-and-coming comedians and big-name stars. On some nights, audience members can even test their improvisational chops onstage alongside real UCB performers. Like the Chelsea theater, comics such as Aziz Ansari and Louis C.K. often pop in for surprise sets, but unlike in Chelsea, UCB East serves pitchers of beer.
12:22 A.M. If you’ve been to New York in the past eight years, chances are you’ve heard about The Box, a secretive nightclub and variety show on the LES. The unmarked building on Chrystie Street (between Stanton and Rivington) isn’t so hard to find anymore, but it’s still an amusing place to watch raunchy burlesque in Manhattan. Reserve a private table and arrive by midnight for the steamy, nude performances that begin at 1 a.m. Acts rotate regularly, so you never know what to expect in the 7,000 square-foot theater. Black tie is extremely optional.
3:19 A.M. Late at night the handsome gastropub Hill & Dale turns into a hopping 1930s-themed lounge. Antique gramophones and phonographs are stuffed into every corner of the parlor-like space, and DJs play crowd favorites from multiple generations. Saddle up to the bar and order Americana delicacies such as deviled eggs, house-made chicken nuggets, and the NYC drink du jour: gourmet peach-and-vodka Jell-O shots.
4:30 A.M. A few things in life are certain: Death, taxes, hangovers and that Veselka will be open. The 24-hour diner—a favorite hangout of locals, celebrities and local celebrities—has been dishing out Ukrainian comfort food from the East Village since 1954. You must try the crispy potato pancakes and beef borscht, a tangy, blood-red beet soup. Order the short rib pierogis, which are served with sautéed onions, sour cream and applesauce, and the cabbage stuffed with beef, pork and rice, and drenched with mushroom gravy or tomato sauce. Just like the Lower East Side grandmothers living in tenements used to make.
Alyson Sheppard is a contributing editor at Playboy.com. Her work has appeared in Maxim, Popular Mechanics, Mental Floss, McSweeney’s, National Geographic Adventure, and more. Follow her on Twitter @amshep