cocktail at Oscar Wilde bar in NYC

As one of the world’s top nightlife capitals, New York City’s got some pretty cool bars. But sometimes, you crave a place that offers something more than a fancy cocktail and a dark-and-sexy vibe—you want to visit a bar that has distinguished itself with something truly intriguing. Perhaps it’s the highest rooftop to drink a martini, a speakeasy tucked behind an ice cream parlor, or a dive that’s tried to hide a controversial past.

Whatever you’re looking for, you’ll be able to drink it up at one of the city’s most fascinating bars. Here are 8 local bars with some downright captivating facts you can use to impress your drinking buddies.

Oscar Wilde

Oscar Wilde bar NYC

Oscar Wilde

At nearly 120 feet long, the bar at Oscar Wilde is reputed to be the longest in the city. But that’s just the start of what’s interesting at this beloved bar. It also has 26 antique clocks, all set to 1:50—the time of the namesake Irish playwright’s death. A nearly 200-year-old player piano comprises the back of the whiskey bar. And those one-armed chairs aren’t a defect—they were designed to remind guests of the Irish exit.

SkyLawn

SkyLawn rooftop bar NYC

SkyLawn

The rooftop bar atop the Embassy Suites by Hilton in Midtown is all about great views—not only of the Empire State Building, but also iconic movies displayed on one of the largest outdoor movie screens in Manhattan. Grab a cocktail created by New York Distilling Company mixologist Allen Katz and settle in to one of SkyLawn’s comfy deck chairs for the show.

Castell

Castell rooftop bar NYC

Castell

The AC Hotel’s rooftop bar, Castell, might be best known for its classic cocktails and meticulously made martinis, but it’s the only place the five boroughs that has a salted grapefruit paloma on draft. The refreshingly tart drink is a subtle celebration of the bar’s Spanish influence.

King Cole Bar

King Cole Bar NYC

King Cole Bar

Secrets abound at the King Cole Bar. The lush lounge in the St. Regis is the birthplace of the Bloody Mary. But the invention of everyone’s favorite brunch-time tipple isn’t the only fun fact about the King Cole Bar. Take a closer look at Maxfield Parrish’s massive “Old King Cole” mural behind the bar. Wondering why the jesters seem to be holding back giggles? Rumor has it that King Cole just cut the cheese.

The UES

The UES speakeasy NYC

The UES/Facebook

The UES on the Upper East Side looks like your trendy ice cream parlor du jour, with its Millennial-pink entryway and light-up cone sign. But most of the guests lining up outside aren’t waiting for a scoop of vanilla—they’re planning to slip past the wall of 180 empty ice cream cartons next to the counter into one of the city’s newest speakeasies.

McSorley’s Old Ale House

McSorley’s Old Ale House NYC

McSorley’s Old Ale House

NYC’s oldest continuously operated saloon has been an institution in the city since 1854. But did you know that it didn’t welcome women for more than 100 years? In fact, Dorothy O’Connell Kirwan, who owned the bar from 1939-1974, only visited on Sundays after closing time. Even though a lawsuit forced the bar to end its ban on ladies in 1970, it didn’t install a women’s restroom until 1986. Nowadays, you’ll find members of both sexes savoring “dark” or “light” ale (the only two beers on draft) while kicking around the sawdust that covers the floor.

Fine & Rare

Fine & Rare bar with live music NYC

Fine & Rare

Want to experience the romance of Grand Central Terminal without the bustling crowds? Slip into Fine & Rare, where you can see antique brass teller windows from the beloved train station. Continuing the theme of interior design that celebrates the past, the doors to the private room are actually from a Masonic Temple. The spot regularly hosts live music—you can even hear Lady Gaga’s go-to trumpeter, Brian Newman, on Saturday nights.

The Flatiron Room

The Flatiron Room NYC whiskey bar

The Flatiron Room

The Flatiron Room woos whiskey wonks with a menu of more than 1,000 variants—one of the largest lists in the world. Should you wish to buy one of the rare bottles, you’ll be able to participate in the bar’s Bottle Keep program. It allows you to store the bottle at The Flatiron room and access it via a special card. It’s like your own personal pirate booty right in Manhattan.

Related Video: Behind the Bar with Matt Seigel

Header image courtesy of Oscar Wilde NYC.

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