Inside The 'Mad Men' Cocktail Tour

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. 

 

People who want to take their own Mad Men walking tour can find plenty of information online about which buildings, bars, and restaurants to visit. There are countless sites and resources discussing Mad Men's New York City places, but Sidewalks of NY offers — for now at least — the only guided Mad Men walking tour.

The tour is not for the faint of liver. Included in the $150 ticket price are three cocktails at bars carefully selected to capture the essence of the show. Everyone is free to order what they want and to get additional drinks or food, but Doyle suggests drinks that honor the Mad Men experience. At the Oyster Bar, it's a nicely understated version of a Tom Collins — gin, lemon juice, sugar, and seltzer.

New York is said to be the most filmed city in the world — surpassing even Los Angeles — so it is logical that tours would spring up to capitalize on popular TV shows. There are Sex and the City, Sopranos, and Gossip Girl tours, as well as dozens of more obscure ones, and there are companies like OnLocation.com that specialize in film and TV tours exclusively.

"The Sex and the City tour was a million dollar idea," says Hirsch. "We're hoping Mad Men will be the next one."

The New York City tourism market is competitive, especially for niche tour companies. "We're all competing for the same tourists to sign up for our tours," says Hirsch. "Tourists have so many options in New York. They can choose between a bus, boat, or walking tour, and the bus and boat tour companies have large advertising budgets."

There are currently 212 different New York City tours listed on TripAdvisor. "This isn't even taking into account other activities like shopping, museums, shows, live music, and sporting events," says Hirsch.

Food tourism has also exploded. According to Foodtourpro.com, a web site that helps companies set up and manage tours, around 16 million Americans annually choose their travel destinations based on food alone.

"Even if visitors decide they want to try a walking food tour, in New York City they can choose from around 10 different companies," he adds.

Hirsch runs Sidewalks of NY from his home office on nearby Greenwich Street. "I like to say I went from Wall Street to walking the street," says Hirsch, who worked as a day trader through the 1990s and 2000s. In 2008, when the S & P 500 dropped from 1400 to 800 points, Hirsch made a long bet on the market improving, but ended up losing everything when it dropped another 150 points.

"I was broke and had to pick myself back up, dust myself off, and figure out what I wanted to do for a living." Hirsch founded Sidewalks of NY two years ago.

Doyle, a 27-year-old Columbus, Ohio, native, is an actor and stand-up comedian who worked on New York City bus tours to pay the bills. About a year ago, he emailed Hirsch asking if he was hiring. Luckily, he was.

Doyle isn't just a Mad Men expert — he is also a qualified New York City tour guide, certified by the Department of Consumer Affairs. Doyle's qualification comes in handy on the Mad Men tour, where he can speak with as much authority about New York neighborhoods and history as he can about Mad Men gossip and trivia.

 

The second stop on the Mad Men drinking tour is the Roosevelt Hotel — the "grand dame of Madison Avenue" and a very short walk from Grand Central. The Roosevelt and has some very impressive Mad Men credentials: In the 1960s, coinciding with the show's timeframe, the Roosevelt was owned by Conrad Hilton, who lived in the hotel's penthouse. On the show, Hilton's fictional counterpart hires Don Draper to market his New York hotels. Don Draper lived at the Roosevelt when he separated from his wife, and its bar has been featured in numerous other scenes.

The Roosevelt has recently started capitalizing on its Mad Men link, hosting viewing parties and offering the Mad Men tour group some special deals. The hotel's bar has some interesting original cocktails, like the Root Beer Float: root beer vodka, vanilla vodka, and ginger ale. The tour guests are tempted, but decide to stick with more Mad Men-appropriate options, and order dirty martinis and London Easts — a gin cocktail with Indian spices.

The final location for the night is a pleasant 10-minute walk uptown to P.J. Clarke's on Third Avenue, which is featured several times on the show.

"P.J Clarke's is where Buddy Holly got engaged, and Frank Sinatra said it was the best place in the city to end a drinking session," says Doyle.

P.J. Clarke's opened in 1884, and has resisted the tide of high-rise development in the neighborhood, making it a historical curiosity. The red two-story building sits stubbornly among glass skyscrapers, and the interior hasn't changed much either. The restaurant frequently features on "Best Hamburgers in New York" lists, and the group orders a bunch, along with the Mad Men drink of choice, an Old-Fashioned  — Maker's Mark bourbon, muddled sugar and bitters, and crushed maraschino cherries.

Hirsch and Doyle's tour concentrates on Midtown and the Upper East Side of Manhattan, but there are plenty of other locations in Manhattan ripe for the Mad Men experience. Doyle has plenty of suggestions for neighborhood-specific Mad Men tours or bars, like the Minetta Tavern in Greenwich Village.

Of course, many New York bars featured on the show — like Chumley's, an old speakeasy, and the Gaslight Café — have long since closed. This is not surprising in a city where new bars and restaurants frequently fold after just a few months. The good news is plenty of other Mad Men bars are still open for business.