Whiskey Bar Time Machine: 5 Historic NYC Hotspots

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New York is a city with a past, and to dive into its depths, sometimes you don’t need a museum; you need a bar. Preferably a storied, ancient whiskey bar with character in spades. Transport yourself back in time with these one-of-a-kind whiskey bars and experience the aura of old New York – from the grandeur of Mad Men-style dining rooms to the shady allure of Prohibition-era ateliers.

Living History

When you step into Fraunces Tavern – part museum, part restaurant – you’ll feel like you’ve wandered into colonial times. There’s a reason for that: George Washington once gave a speech here. The landmark tavern’s wide-planked floors and crackling fireplaces transport you straight to 1700s New York. Inside, head for the Dingle Whiskey Bar, a wood-paneled haven offering a wide selection of whiskeys, and for connoisseurs, there’s the members-only Fraunces Tavern Whiskey Society.

Cocktails and Cuts

Keen’s Steakhouse is certifiably old school, dating back to the time of Teddy Roosevelt, whose personal pipe (along with Babe Ruth’s and Einstein’s) is one of the 40,000 clay churchwarden pipes suspended from tiny hooks covering the restaurant’s ceiling. The landmark steakhouse has been serving up prime cuts since 1885. Choose from one of 200 single-malt Scotches, then roll up your sleeves, tuck your napkin under your chin, and dig into a juicy, rare porterhouse.

In Serious Spirits

Velvet curtains, private nooks, and a dizzying list of 1000-plus whiskeys are just the beginning at the Flatiron Room. This is the destination for true whiskey enthusiasts. Live bluegrass and jazz and leather banquettes evoke a loungey, old New York ambiance. If you’re looking to learn something new, the Flatiron Room’s whiskey school offers in-house classes and tastings. Bar bonus: Here, you can buy a bottle without the stress of emptying it in one go; the Flatiron’s “bottle keep” will tag and store your favorite whiskey for a future visit.

Malts, Music… and Murder?

When you step out the elevator, be ready to shed your inhibitions and break the fourth wall. The Heath is as much an experience as it is a restaurant and bar – mainly because it’s located in the McKittrick, a fictional hotel whose labyrinth of elaborately designed rooms serves as the set for the popular immersive theater production, Sleep No More (also highly recommended). Though the restaurant isn’t part of the performance, it’s a fitting pre- or post-show destination; at the McKittrick, the magic is the ambiance. The Heath is laid out like a Prohibition-era dinner club, with live jazz and mysterious, costume-clad figures weaving through the hazy room. You may even be plucked from your table to participate in an eerie adventure.

The Gilded Age

Leave the tea party to Eloise and channel your inner Rockefeller at the recently renovated Palm Court at the Plaza Hotel, where you can now sip sophisticated cocktails into the evening under the room’s iconic stained-glass ceiling. Celeb chef Geoffrey Zakarian is behind the new plates and cocktail menus, which are as pricey and decadent as you’d expect from the Plaza’s classic grandeur, marked by statuesque palm trees and gleaming chandeliers. If your pockets are feeling as deep as Gatsby’s, take the plunge with the Palm Court’s $225 Manhattan.

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