Gramercy Opened: 1864 Surviving the Depression and two World Wars means Pete’s Tavern was established in 1864, and even stayed open during Prohibition, when it masked itself as a flower shop while still serving alcohol. Initially called Healy’s Cafe, the place didn’t get the name Pete’s Tavern until Pete Belle purchased the property in 1932. Sidle up to the intricately carved rosewood bar, and order one (or four) of the house special, the 1864 Original House Ale. Fun fact: O. Henry, who lived close by, wrote The Gift of the Magi here in a booth.
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East Village Opened: 1862 While the exact year McSorley’s opened is still up for debate (the sign outside reads 1854, but historian Richard McDermott claims it opened in 1862 based on public records), one thing is certain -- this over-a-century-old, cash-only, beer-only Irish ale house is really freaking old. Like, Lincoln, Babe Ruth, and Teddy Roosevelt beer’d it up here old. And because two beers are better than one, suds are served in pairs of seven to 8oz glass mugs. Just memorize two words: light and dark. It’s the only type they offer. Fun fact: McSorley’s started out as a major bro fest -- their motto used to be “Good Ale, Raw Onions, and No Ladies”. It wasn’t until 1970 that women were allowed in (by court order).
Tribeca Opened: 1817 More than a century ago, this Soho watering hole was a hotspot for sailors waiting for their ships to dock. Built in 1817 for James Brown (no, not that one), this watering hole didn’t get its name until 1977, when the neon “BAR” sign was painted to read “EAR” (after a music magazine that was published upstairs). It’s said a sailor ghost named Mickey pops in every now and then for a drink. And probably one of their excellent burgers. Fun fact: Legend has it this historic bar didn’t serve drinks until the 1890s, when an Irish immigrant, Thomas Cooke, bought the place and began brewing beer and whiskey to serve seamen. The location has, at one point or another, done time as a boarding house, smuggler’s den, and even a brothel.
Financial District Opened: 1762 Samuel Fraunces purchased the property in 1762 from the Delancey family (who was living there), and converted it into a tavern called the Queen’s Head. It’s now part-bar, part-restaurant (you can order everything from steak to colonial-style shepherd’s pie), part-whiskey bar, and part-history museum. Earn some cool points by getting in on one of their booze clubs (Fraunces Tavern Whiskey Society FTW!), then earn some beer points by also raising a glass of Porterhouse Oyster Stout. Fun fact: Picture your first president shot-gunning a beer at this nostalgic bar. Okay, maybe not, but our boy GW was one of its famed customers.
Midtown Opened: 1884 This Midtown tavern has been pouring cold ones since 1884. To put things into perspective, it's been around longer than the Empire State Building and Brooklyn Bridge, and it has the classic tchotchkes to prove it (see: stuffed Skippy the dog, once the bar’s mascot). The bartenders still make a killer Manhattan, and it's worth coming hungry, too -- the signature “Cadillac” burger comes with smoked country bacon and American cheese (plus, it's served until late). Fun fact: Its 150-year resume reads like the ultimate Throwback Thursday list: it’s where Buddy Holly proposed to his wife, Jackie Kennedy brought John Jr. and Caroline for lunch, Johnny Mercer wrote his song “One For My Baby” on a napkin, and Sinatra was to known to cap off his nights regularly.
West Village Opened: 1880 Dating back to 1880 as a hangout for longshoremen, this West Village saloon later became a popular gathering spot for literary lushes like Michael Harrington, James Baldwin, Dan Wakefield, John Ashbery, and Hunter S. Thompson. Fun fact: Believe it or not, Dylan Thomas had his first and last 18 whiskeys here. A popular myth says that Thomas’ ghost haunts his favorite table in the room, where his picture now hangs.
Hell’s Kitchen Opened: 1868 This Hell’s Kitchen survivor first opened its doors in 1868, serving booze to dock workers before the third floor turned into a speakeasy during Prohibition. It was eventually renovated in the early 2000s in the hands of new owners, but it still retains its historic charm, including tin ceilings and an original mahogany bar carved from a single tree. The menu lacks pretty much all pretense, with items like shepherd’s pie, Scotch eggs, potato and leek soup, and fish and chips. And definitely go for the house ale, a hoppy IPA produced by a brewery upstate. Fun fact: The speakeasy hasn’t forgotten its past. Hollywood gangster George Raft’s ghost is said to haunt the bar (it was known to be one of his faves), along with a Confederate Civil War veteran and an Irish lassie.
West Village Opened: 1840 First holding court as a grocery in 1840, then as a bar in 1864, today it’s one of the city’s oldest gay bars. Signs of old-age point to the ancient newspaper clippings and wall covered in signed head shots. It’s also the site of the 1966 Sip-In, where a few activists challenged the NYS Liquor Authority’s regulation that prohibited bars and restaurants from serving homosexuals. Real-talk: the best-kept secret at this joint is their juicy $6 burgers. Get the namesake with greasy onion rings. Fun fact: Tennessee Williams and Truman Capote were both fans.
Flatiron Opened: 1882 Before Old Town Bar was Old Town Bar, it was known as Viemeister’s in 1882, and later as Craig’s Restaurant -- a speakeasy during Prohibition. Old Town first opened as a saloon liquoring up only dudes (again with this). Today you can pull up a seat at the 50-plus-ft mahogany bar, and grab some of the city’s top wings. Soak up the suds with a chili dog delivered to you via an antique dumbwaiter. Fun fact: Break the seal in a 102-year-old urinal in the boy’s room. Seriously -- this might be the only time you leave a bathroom thinking, “Hmmm, that was kinda cool”.
Little Italy Opened: 1908 Formerly called Mare Chiaro, this Little Italy bar (which opened in 1908) pays homage to its early days with an original subway tile floor, wooden bar, and tin ceiling. In 2003, Ed Welsh bought the digs to “have a place to drink for free”. Smart guy. A jukebox playing Sinatra and Elvis provides the soundtrack, and weekends bring karaoke. They had karaoke in 1908, right? Fun fact: If you’re ever looking to take a mobster for a night out on the town, this place is it. You might recognize the spot from Donnie Brasco, Men of Honor, and The Sopranos.
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Alisha Prakash is a contributing writer at Thrillist NYC. Her mission: make Sriracha a food group. You can find more of her musings on her website or follow her on Twitter.