7: Old Town Bar (Flatiron District)
45 E 18th St, between Broadway and Park Ave, www.oldtownbar.com
Take a trip back to the Victorian era at this atmospheric bar popular with publishing types and photographers (the Tumblr offices are nearby). Though it opened in 1892, much of the creaking interior is original, including the rickety dumbwaiter, the handsome 55-foot (16.7m) mahogany and marble bar and the monstrously large urinals in the mens' bathroom, fitted in 1910.
Happy Hour: None
Drink this: Blue Point Toasted Lager (US$7)
Next move: Not far this time. Walk a block and half east along 18th Street (3min).
8: Pete’s Tavern (Gramercy)
129 E 18th St, www.petestavern.com
Who exactly was O. Henry? Open since 1864, this former speakeasy now trades unashamedly on its history, which has included such illustrious patrons as O. Henry – it’s just a shame that no one other than NYC lit majors really knows who O. Henry was (the poet wrote “The Gift of the Magi” here in 1904, allegedly – pretend you’ve read it). This is also another place that has a focus on food, but the old bar, with 16 beers on tap, drips with nineteenth-century atmosphere.
Happy Hour: None
Drink this: 1864 House Ale, or Pabst (seriously, on draft!); US$7
Next move: Walk back to Union Square (5min) and take the 4 or 5 express to 59th Street (6min); then walk 4 blocks south (5–10min).
9: PJ Clarke’s (Midtown)
915 Third Ave, at E 55th, www.pjclarkes.com
Finally, here’s one Midtown pub within stumbling distance of your Times Square lodgings that has some historic pedigree. Built in 1868 (though the exact date is still disputed), the bar opened around 1884. Mr. Patrick Joseph “Paddy” Clarke purchased it in 1912, and it’s been a regular for a bevy of stars ever since, from Elizabeth Taylor and Richard Harris to Jackie Kennedy and Nat King Cole.
These days its wine selection is better than the beers, though the infamous burger, served with a pickle and a slice of raw onion, is still one of the best in town.
Happy Hour: None
Drink this: Brooklyn Lager or Goose Island (US$6)
Next move: Grab a taxi for the final switch across to the west side (11th Ave at 46th St); US$6.50; 5–10min.
10: Landmark Tavern
626 Eleventh Ave, at W 46th St, www.thelandmarktavern.org
Off the beaten path in Midtown’s western industrial wasteland, this long-established Irish tavern (opened in 1868) offers decent Guinness, shepherd’s pie and Irish soda bread baked fresh every day. Note the sturdy bar, built from a single mahogany tree, and the original speakeasy front door. By this stage of the tour you may well start seeing one of two ghosts said to haunt the pub: a young Irish girl who died on the third floor, and a Confederate soldier who was mortally wounded in a drunken brawl and also passed away upstairs.
Happy Hour: None.
Drink this: Smithwick’s (US$6).
Next move: Landmark is four (but long), stumbling, blocks west of Times Square, where the Disney Store is open till 1am – I’m just saying.
NB: Since the time of writing, the more pub-like Paris Café (1873), another one of the oldest watering holes, has recently been renovated and reopened in the wake of Hurricane Sandy.
Stephen Keeling is the co-author of the Rough Guide to New York.