Inside the 'Mad Men' Cocktail Tour

The New York City tour hits some of the show's favorite watering holes

One cool April evening at 7 p.m. sharp, a young blond man dressed in a 1960s tie and cap meets six strangers under the clock in Manhattan’s Grand Central Station. After a few minutes, the man, clutching a distinctly non-‘60s era iPad, shepherds the group through the remnants of the rush hour crowd and downstairs to the Oyster Bar. They drop anchor in the back saloon, where the man orders a round of cocktails.

The bar, located on the station's lower level, is the first stop on the Mad Men cocktail tour, an evening spent in watering holes featured on AMC’s hit drama. The man in the tie, Kevin Doyle, is the guide. Each tour takes between two and 12 people, and Doyle’s guests for the evening are the Mitchell family from St. Louis — avid Man Men viewers.

The station’s main concourse is a natural starting point. In the show’s early seasons, the main character, Don Draper, rides the commuter train from Ossining, N.Y., to Grand Central every day. The Oyster Bar, which opened in 1913, is a culinary landmark as well as an architectural throwback, with distinctive vaulted, tiled ceilings. The Oyster Bar also has an impressive wine and cocktail list.

A few months ago, Doyle sat at that same saloon bar with his friend Josh Hirsch, drinking gin martinis and plotting suitable destinations for the Mad Men experience. Hirsch is the founder of Sidewalks of NY, a walking tour company specializing in food and historic neighborhoods.

The show’s producers, and its viewers, are sticklers for historical accuracy. Period-appropriate clothes, food, products, and slang are researched by experts, and then closely monitored by fans and critics.

"Except for the pilot, Mad Men is shot in LA, so we were researching how faithfully the real-life bars have been reproduced on the show." says Hirsch. They used Doyle’s iPad to check the show’s New York sets against the real-life venues. "We were watching the scene in the Oyster Bar when Don Draper and Roger Sterling have six martinis and a bunch of oysters for lunch, and it was all there," says Hirsch. "Down to the red-and-white checkered tablecloths and the small martini glasses, which are about half the size of the ones you’d find in most New York bars today."

Mad Men’s New York is brought to life through its bars and restaurants; it would be too expensive to create 1960s period shots of New York City week after week. "Because the show is shot in LA, it’s difficult to do a traditional walking tour of filming locations." says Doyle. "So we decided to do it at night, in bars, and make it more of an experience."

He adds, "We chose places that are very old New York, where you walk into them and they don’t feel like 2012 at all." The tour stops are also within easy walking distance of one another, with plenty of Midtown New York to see in-between. After one drink in the Oyster Bar’s saloon, Doyle herds the group out of the terminal and onto Madison Avenue.