25 Ways To Do New York Like Mad Men's Don Draper

Much like certain episodes of Seinfeld or a good Woody Allen movie, in many respects, New York City itself was one of the greatest characters on Mad Men. Sure, Don Draper was a mystery wrapped in a riddle, Peggy Olsen was a feminist trailblazer, Roger Sterling was a hilarious jerk, and so on and so on, but it was the Big Apple that brought all these characters together. More importantly, nowhere else in the world could such an eclectic group be united by the power of advertising, both greedily and artistically wanting to suck every dollar out of the big city’s pockets through the beautiful power of commerce.

Recognized for it’s verisimilitude and respect for history from the very beginning, Mad Men was very aware how much NYC meant to the show, turning many episodes into low key tributes to the real location. Ironically, most of the series was actually filmed in Los Angeles, yet through painstaking effort, dozens of New York landmarks were perfectly recreated so Don and his friends could cut deals and raise hell in them like only they could.

Quite frankly, given how reckless Draper and company could get at times, setting out to be just like them might be a little bit dangerous to a person’s health. That said, anyone who thinks they know how to play it safe should keep reading for 25 ways to do New York City like Don Draper and the cast of Mad Men.

25 Late-Night Show

via Twitter

There’s no shortage of options for a person seeking late night entertainment in New York City. In an effort to cheer up Lane Pryce one night, Don Draper checks out two of the city’s offerings with a silly B-Movie called Gamera, The Giant Monster followed by a trip to a comedy club where they meet some rather friendly ladies. Obviously, it’s going to be a bit hard finding a theater playing Gamera, well, anywhere on Earth, but NYC will always be one of the top locations around for stand-up. While Don was just there for the females, anyone actually looking to laugh will definitely find what they need.

24 Go On a Studio Tour

via realclearlife.com

Because Mad Men was filmed in Los Angeles, fans won’t actually get to tour the studios in which the show was made in New York City. That said, there are plenty of other shows being made in the Big Apple, and those created by larger companies often offer studio tours that any fan of TV or film should enjoy. Technically, Don Draper never went on such a journey, but he was indirectly involved in the creation and casting of a few TV ads thanks to his pal Harry Crane. Taking things full circle, this eventually brought parts of Sterling Cooper Draper Pryce to LA, where their budding television empire expanded.

23 Dine at Sardi’s

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One block away from Broadway, the iconic Sardi’s restaurant has long been a top hangout for celebrities and their supporters. To reflect this fact, the location features wall-to-wall caricatures of virtually every celebrity to pass through its doors. Recently, none other than John Slattery, a.k.a. Roger Sterling, became one of the famous faces drawn in a silly and memorable way. Of course, that particular drawing wasn’t there when Don Draper and his umpteenth side lady Bobbie Barrett chose Sardi’s as the spot to celebrate her husband’s new show Grin and Barrett. When mimicking their encounter, make sure to pay attention to the road on the way home.

22 Spend a Night at The Pierre

via Prashanti

New York City has no shortage of hotels, and The Pierre is renowned for being one of the most luxurious. For this reason, it might be out of the price range for the average world traveler, but the biggest Mad Men fans have a pretty good reason to spring for the expense—specifically, suite 435. During the transition period from Sterling Cooper to Sterling Cooper Draper Pryce, the usually-spacious area became the rather cozy temporary home for Don Draper and his coworkers as they did their business. Ironically, while it was just another room back then, it’s now the location of an actual executive meeting room.

21 Eat a Bunch of Oysters (But Not Too Many)

via Food and Drink International

Any fan of Mad Men looking to eat a bunch of oysters should immediately know that moderation is pretty important to the idea. Unfortunately for Roger Sterling, they learned this lesson through his mistakes after he and Don Draper visited the Grand Central Oyster Bar and Restaurant. In an early moment of male bonding, the two ad men drank and ate an exaggerated amount of shellfish, only to get back to the office and find the elevator was out of order. Combined with their indulgent meal, climbing the stairs up several floors caused Roger to completely lose his lunch all over the shoes of a few very important clients.

20 Spring for the Hotel Elysée

via National Trust for Historic Preservation

Being permanent residents of New York City, when the cast of Mad Men needed to stay at a hotel, it wasn’t always because they were on vacation. Of course, the average person shelling out the big bucks to stay in a luxury location like the Hotel Elysée is probably going to use their room for longer than Peggy Olson and Duck Phillips used theirs in “Seven Twenty Three.” Rather than stay in bed all the time, guests will probably also find the time to check out the hotel’s famous Monkey Bar, which was also seen in the shows Sex and the City and Younger.

19 Hang Out at the Club (in a Couple of Months)

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Technically speaking, no one can ever again visit the Playboy Club as it was seen in Mad Men, since the original location closed down in the '80s. However, the extremely-exclusive hot spot known primarily for gorgeous waitresses dressed as sultry hares is rumored to be making a comeback very soon, with Playboy poised to open a new Manhattan location sometime in the near future. Hopefully, residents won’t fall down the same rabbit hole as SCDP name partner Lane Pryce, who became a frequent patron to the Club after falling in love with one of those attractive waitresses while still married to his wife.

18 Watch an event at Madison Square Garden

via AnyFlip

In order to succeed in advertising, one needs to have their finger on the pulse of social trends and pop culture. The executives of Mad Men make several efforts at doing this, with Don and Harry once catching a Rolling Stones concert, and just about everyone else in Sterling Cooper getting tickets to witness the second legendary boxing match between Sonny Liston and Muhammad Ali on closed-circuit TV. Although neither of these events took place at Madison Square Garden, anyone in the real Big Apple looking for a similar rock and roll or athletic experience couldn’t pick a more famous arena in which to have it.

17 Eat at The Palm

via popsugar.com

Speaking of Liston-Ali, before the staff of Sterling Cooper sits down to watch history, many of them prepare with a hearty meal at The Palm. Heralded as “the place to see and be seen,” everyone seems stoked about the one-two punch the experience offers except Don Draper, who apparently wants to see the fight literally anywhere else except the location his coworkers are eating. Obviously, the average diner won’t have this aversion to such a famous location, and might feel more inclined to mimic the feelings of Trudy Campbell, who gleefully chows down on a rare steak while getting ready to watch “two men pound each other.”

16 Experience the Brightly-Colored Glory of Times Square

via Time

A brisk 9 minutes away from Madison Avenue, its a bit surprising Don Draper nor any of his coworkers ever had a scene where they wandered through Times Square. Covered in extremely bright neon advertisements everyone a person looks, chances are some of their more prominent work was displayed in the major hub for food and entertainment. Even though the cast of Mad Men never visited the area, it will soon be the perfect place for fans to try and act like their favorite characters, as Lionsgate Entertainment has chosen Times Square as the location for a themed restaurant after the show, set to open sometime in 2019.

15 Get Fancy at a Country Club

via Style and Cheek

Truth be told, this entry may be hardest to pull off for the average tourist. Most New York City country clubs are both highly exclusive and expensive, many of them adopting strict invite-only rules. That said, anyone with the right friendly connections would likely enjoy seeing how the wealthy elites of the Big Apple get to relax and enjoy themselves. Thankfully, modern social morays mean there won’t be any performances like Roger Sterling’s offensive display, but it’s entirely possible to meet some important people at such an establishment, similar to how Don Draper met the extremely wealthy Conrad Hilton, or how his first wife met her second husband, Henry Francis.

14 Walk Near the Offices of Sterling Cooper Draper Pryce

via Time

Such is the nature of fictional television that Mad Men fans unfortunately won’t be able to visit the offices of Sterling Cooper Draper Pryce, what with the pesky fact that the company never actually existed. On the plus side, the Time Life Building where Don Draper’s second office was located was indeed a real place, and today, it’s known as 1271 Avenue of the Americas. Unless someone is looking for office space, they may not find much to do in that particular building, but the location is now within the much larger Rockefeller Center, which offers plenty in the way of food and entertainment a tourist may find interesting.

13 Watch a Performance at a Coffeehouse

via The Gaslight Cafe.

Movies, arenas, and comedy clubs are all great ways for a NYC tourist to get entertained, but someone looking for a more intimate environment may want to look into a smaller coffeehouse meant for quiet poetry or similarly quiet performances. In Mad Men, Don Draper and one of his ladies named Midget Daniels venture an establishment like this in The Gaslight Cafe. Unfortunately, this particular coffeehouse closed in the '70s, but it was hardly the last bastion for folk music and beat poetry in the Big Apple. Which one best suits a given trip to the city likely depends on their specific schedules, which any interested parties would do well to research.

12 Swim and Sunbathe at Jones Beach

via iloveny.com

For all the commerce and commercialism that makes New York City famous, the borough of Manhattan, where most of Mad Men takes place, it also has the perks of being on the coast. This means there are plenty of beaches in the area, any of which would be a good place to relax during a hot summer trip. While audiences don’t see much of the fun in the sun part, they learned Peggy Olson and her friend Joyce have enjoyed Jones Beach in particular. It turns out Abe Drexler is also a fan of the spot, accidentally running into Peggy there for a second time and kicking off their long relationship in earnest.

11 Have a Steak at Keens

via wennermedia.com

Hopefully it goes without saying that no matter how into Mad Men a person is, smoking is always an unhealthy choice, so a wealth of cigarettes shouldn’t be included in a trip to New York City or anywhere else. That said, we can’t pretend smoking isn’t an integral part of the show, so perhaps fans could get their fix just by heading to Keens Steakhouse, home to a massive collection of antique pipes. More directly related to the show, it was also the site of a dinner meeting between Don Draper, Pete Campbell, and Horace Cook, Jr., who spent the entire meal trying to sell the others on jai alai.

10 Learn All About Natural History

via AMC

While this list is mostly about fun, food, and fancy accommodation, one can’t forget that New York City is also home to some of the best museums and historical artifacts in the world. Tourists interested in the city’s intellectual side would do well to check out the American Museum of Natural History or any other educational institution the city has to offer. Apparently located quite close to the Francis residence, that specific museum was the location for a date of sorts between Sally Draper and her friend Glen Bishop. It also became a huge part of Sally’s personal growth, as it was where, in the words of her mother, she “became a woman.”

9 Experience the Chisholm-Larsson Gallery

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For those who feel like a natural history lesson and a New York City vacation don’t quite go together, there are plenty of other museums with unique exhibits that may catch a tourist’s eye. In addition to the always-unique Museum of Modern Art, there’s also the Chisholm-Larsson Gallery, dedicated entirely to vintage posters of all kinds. Don Draper never advertised a movie, but if he did, his theoretical designs would surely fit right in amongst real classic movie promotions of his time period.

8 Check Out the Waldorf-Astoria

via chron.com

Every hotel in New York City has its perks, yet the most famous of all may well be the Waldorf-Astoria. As Conrad Hilton himself tells Don Draper in Mad Men, it’s the one lodging famous enough to have a salad named after it, along with plenty of other high-end dining options and accommodations in general. Unfortunately, at the time of this writing, the iconic building is currently closed for an extreme renovation that’s poised to continue for at least two years. While this means no one can stay there for some time, even passing by the building and thinking about what it means could feel historic to a big fan.

7 Go Shopping at Bloomingdale’s

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Easily one of the most commercial cities on the planet, the Big Apple includes an uncountable number of incredible shopping hot spots, and only someone with endless credit cards can really experience them all. For a Mad Men fan, looking to keep it simple, the one location to hit would probably be Bloomingdale’s (if only because Menken’s isn’t real). While there’s no evidence Don Draper himself shopped there, Pete Campbell was forced to return the second “chip 'n dip” he and Trudy received at their wedding. Because he had no receipt, the store refunded him with credit, which he used to buy a weapon. Maybe don’t try that part at home.

6 Do the Twist at P.J. Clarke’s

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Most 24-hour party people visiting New York City for the first time are probably going to look for the hippest night club in town to spend their wildest evening. Then again, Mad Men fans take a decidedly throwback approach to a good time, so they may prefer P.J. Clarke’s, one of the oldest watering holes in the Big Apple, which still adheres to traditional forms of celebration. In addition to a retro design, the jukebox is still loaded with '50s icons like Frank Sinatra and Chubby Checkers. The classic rocker was on the menu when Peggy Olson rocked out and celebrated a successful pitch to Belle Jolie, getting funky to the sounds of his iconic single “The Twist.”

5 Stay overnight at the Roosevelt (or Rent a Room For a Few Weeks)

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Slightly more affordable than some of the other hotels on this list, the Roosevelt is no less iconic in it’s own right. Proving how luxurious it truly was, hotel impresario and low-key Mad Men character Conrad Hilton chose the Roosevelt’s Presidential Suite as his long-term residence, and one of his fictional friends had a similar idea. Granted, it wasn’t exactly Don Draper’s choice for his wife to catch on to the many relationships he was having and kick him out of the house, but still, it says something that he picked this location as his temporary home when she did so.

4 Head to Coney Island

via slate.com

Contrary to every other example on this list, not only does the cast of Mad Men never venture to Coney Island, but one episode actually features a sly reference explaining why they specifically avoid it. When Peggy Olson catches Dawn Chambers trying to sleep at SDCP, the secretary explains she doesn’t want to travel alone at night due to rampant rioting, referring to a scene in 1966 when angry teenagers raised havoc in Bed-Stuy and the island. Of course, those incidents are long over today, with the location back to being the hub of entertainment it once was. With the fighting over, Don Draper himself may have enjoyed the ferris wheel.

3 Enjoy the Night Life

via Hollywood Reporter

Even without a list, anyone who's seen a single episode of Mad Men probably knows how Don Draper enjoys the average evening away from his family. When mimicking these more indulgent behaviors, it should go without saying that moderation is key, but that doesn’t mean tourists can’t still have a good time. Whether choosing one of our named locations or just indiscriminately going out on the town, it’s important to remember Don’s hangovers along with his more fun experiences. So long as everyone keeps this in mind, New York City’s night life could lead just about anyone to a good time.

2 Meet New People and Go with the Flow

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Quite frankly, it’s hard to imagine Don Draper would ever follow a list like this one. Even if he used it as a reference, the impulsive, freewheeling adman would probably ditch his plans the first time a stranger suggested he do so. Now, it’s not at all a good idea for a tourist to say yes to every random person they encounter, but a huge part of what makes New York City so great is the people who live there. No matter which of our advices one chooses to follow, it’s highly suggested they talk to the locals and experience the Big Apple on their own terms, even if it means tossing out the itinerary for a while.

1 Spend Time on the Real Madison Avenue

via Learning to say nothing

Ultimately, anyone heading to New York City to experience the Mad Men vibe would probably like to go directly to the source and check out the original offices of Sterling Cooper. The problem there is that the alleged address of the building, 405 Madison Avenue, doesn’t actually exist. On the plus side, that iconic street is indeed a real location, and as the show implies, it’s one of the most important stretches of concrete in all of advertising to this day. Fans can’t exactly wander in to random buildings, but they can check out the Advertising Walk of Fame, which commemorates the most successful ad campaigns of all time.

References: NYC Go, Am New York, The Guardian, CNN, Gothamist

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