Photo: Courtesy of Bridge Café

Bridge Café (1794)

THEN

• Clientele: Dock workers, prostitutes, johns

• Popular drinks: Rum, “applejack”, strong beer (6% alcohol), Madeira wine

• Bar talk: New-found freedom from Great BritainNOW

• Clientele: Locals, financial types, politicians, tourists

• Popular drinks: Single malt scotch, wine

• Bar talk: New freedom-limiting Patriot Act

When the Brooklyn Bridge first blocked Water Street from sunlight in 1883, this bar/restaurant had already been serving the local population for almost a century—in more ways than one: An 1860 NYC census lists 279 Water St. as the home of six Irish prostitutes. According to a Times article, the Bridge Café has been a “drinking establishment” since 1847, thus making it the oldest continually running bar in NYC. Only a few blocks from the South Street Seaport, it’s decidedly not a tourist trap. After all, Ed Koch held court here twice a week at his private table during his mayorship, and city politicians still take advantage of its communal but easygoing air to conduct business here over a couple of cold ones. That, and the Bridge Café’s specialties—soft-shell crabs ($15 appetizer/$28 entrée) and whiskey (65 single-malt and small-batch bourbons to choose from, $7.25-$33/glass). For the pence-pinchers, “tastes” of these whiskeys are also available, for roughly one-third the price; beer, wine and mixed drinks start at $5.

Did you know:When it was built, before massive land-fill projects dramatically expanded the surface area of Lower Manhattan, the East River actually came up to the structure’s foundation.

Photo: Courtesy of Ear Inn

Ear Inn (1817)

THEN

• Clientele: Wharf rats, sailors, the unemployed

• Popular drinks: Corn whiskey, home-made beer

• Bar talk: “Is the city really going to build a subway?”NOW

• Clientele: Artists, bikers, professionals

• Popular drinks: Beer, wine

• Bar talk: “Is the city ever going to build the Second Avenue line?”

Only two decades younger but much funkier than the Bridge Café is the Ear Inn (the blacked-out right side of the “B” in the neon “Bar” sign outside gives this establishment its memorable name). To be accurate, the Ear didn’t start serving drinks until the 1890s, when an Irishman named Tom Cloke bought the place from a guy who rented rooms to local craftsmen and their familes. Cloke then turned the place into a rough-and-tumble watering hole for Spring Street’s longshoremen waiting for ships to dock. Nowadays, you’re more likely to run into an artist waiting for work and bellied up to a $5.50 pint and a Moroccan salad—hummus, tabouli, yogurt, and fruit ($7). The wide-planked floor is so old and worn it feels soft under your feet, and the walls and shelves are completely cluttered with art and tchotchkes. Cozy, warm and comfortable, you can spend countless hours eating and drinking here like those longshoremen did a century and a half ago.

Did you know:Charred and axe-marked timber discovered in the Ear Inn’s attic has led some historians to believe the dwelling was constructed partly out of left-over lumber from the great fire of 1776, which wiped out one-third of the city.

Photo: Sandra Nygaard

Chumley’s (1830s)

THEN

• Clientele: Neighborhood, literary giants

• Popular drinks: Whatever was available

• Bar talk: Prohibition infringing on personal libertyNOW

• Clientele: Neighborhood, Eurotrash, Engine 24/Ladder 5 firefighters, tourists

• Popular drink: Beer from Chelsea Piers Brewery, wine

• Bar talk: No-smoking laws infringing on personal liberty

The space is about 175 years old, but Chumley’s is best known for its glory days as a speakeasy during Prohibition. Nowadays cops aren’t trying to shut the place down, but it still retains an element of drama: There’s no sign outside, you have to walk through a curtain to enter, photos of famous writers of the past adorn the walls, and the “secret back exit” that patrons would run through when the coppers used to bust the joint, is still there. Simply put, Chumley’s layout is “really cool.” Multileveled (four different levels to be exact) with booths in the middle, and more booths hidden in the back, you can eat center-stage (portobello burger, $9.50; roast duck, $17); mill about in the bar area’s open space and sample the impressive beer selection ($6 pints); or cozy up in a back booth for some romantic time. Better go on a weekday for the latter, though. Weekends are loud.

Did you know:To “86” someone traditionally means to eject them from a bar or restaurant. Given Chumley’s address of 86 Barrow St., along with its fame as a speakeasy, some etymologists believe the phrase originated here during Prohibition, as a code to customers warning that cops were snooping around.

McSorley’s (1854)

THEN

• Clientele: Men only!

• Popular drink: McSorley’s Ale

• Bar talk: Men only!NOW

• Clientele: Lots of men

• Popular drink: McSorley’s Ale

• Bar talk: Men only!



Though McSorley’s claims it opened its doors in 1854, NYC historian Richard McDermott used public records to prove it really opened in 1862. But McSorley’s is most famous for what happened in 1970 when kicking and screaming it was forced to open its doors to women. This Village mainstay is the last bastion of the liverwurst sandwich ($3), but if gray, pasty meat by-product slathered in mayonnaise isn’t your bag, you can get a cup of soup ($3) or burger ($4.75) and wash it down with light or dark beer. The beers famously come in pairs (i.e., order one, you get two; ask for two, you get four), served in small mugs with almost as much foam in them as the good stuff. The slightest display of confusion will surely betray you as a McSorley’s virgin. “Be good or be gone” is the motto here, although after 26 or 28 of those frothy mugs of beer, it’s a little hard to heed the signs that say as much.

Did you know:The famous poet e.e. cummings penned a poem entitled “i was sitting in mcsorley’s.” In it, he describes the bar as “snugandevil.”

Photo: Courtesy of P.J. Hanley's

P.J. Hanley’s (1874)

THEN

• Clientele: longshoremen

• Popular drinks: locally brewed beer

• Bar talk: 1873 Wall Street collapse and DepressionNOW

• Clientele: locals, sports fans

• Popular drinks: martinis, beer

• Bar talk: Skyrocketing NYC real estate market forcing locals out of the neighborhood

P.J. Hanley’s is where Carroll Gardens’ residents come to drink, watch the Yankees, and debate about when the meatballs go in the sauce. During the 131 years of its existence, the bar has had only four owners, making it not only one of Brooklyn’s oldest bars, but one of the most genuine “neighborhood bars” in the borough. It’s beloved by regulars for its burgers ($6.75), and by big spenders for its T-bone steaks ($23.95). Guinness pints are cheap for NYC ($4); martinis and mixed drinks start at $7. Important note for those in the armed forces: The first drink is on the house for anyone wearing a military uniform. “If Uncle John [the previous owner and WWII vet] ever saw us charge a serviceman,” says co-owner Deborah Hanley, “he’d turn over in his grave.” As for the rest of us, it’s dollar domestic drafts (8 oz.), all night every night. Not bad at all.

Did you know:Red Hook-born Al Capone met his Irish bride in the basement of a speakeasy on Carroll Street and tied the knot a few hundred feet from P.J. Hanley’s, which was formerly a speakeasy called Ryan’s. Could it be that the Godfather of all Godfathers downed some anisettes within these very walls?