Don Draper's New York

Harrison Peck

(Updated 04/03/2015)

Though it's filmed in a Los Angeles studio with minimal exterior shots of vintage New York, Mad Men—AMC's critically acclaimed series that follows fictional Madison Avenue executives in the 1960s—is as quintessentially New York as yellow taxis and pastrami on rye. The show's themes of ambition, reinvention and success—coupled with the glamour, style and sophistication that characterized the early days of advertising—are so closely associated with New York City that the show truly could not be set elsewhere. Though the City's tastes and culture have changed since Don Draper's day—three-martini lunches and desk-side scotch cabinets are, sadly, long gone—the elegance of 1960s New York as depicted on the show has never gone out of style. To prep yourself for the show's final season (whose second half kicks off on April 5 at 10pm ET on AMC), throw on your fedora and step back in time at these glorious relics of Mad Men–era New York, many of which are the hangouts of choice for the men and women of Sterling Cooper. (Though don't waste your time looking for 405 Madison Avenue, the purported address of the advertising agency—it doesn't exist.)

Courtesy, The Pierre New York

The Pierre New York
2 E. 61st St., 212-838-8000
After 80 years in business, the fabled Pierre New York, whose French design–inspired tower presides dramatically over Central Park, remains the epitome of New York luxury and sophistication. And now, after a stunning $100 million renovation, completed in 2009, The Pierre boasts modernized guest rooms, the stylish Two E Bar/Lounge (which serves the hotel's traditional afternoon tea) and the first stateside location of London's renowned restaurant Le Caprice. Initially the site of Don's meeting with department store head Rachel Menken to discuss an Israeli tourism campaign, The Pierre became a central locale on Mad Men in the season three finale when room 435 was transformed into the makeshift offices of new agency Sterling Cooper Draper Pryce.

Courtesy, The Roosevelt Hotel

The Roosevelt Hotel
45 E. 45th St., 212-661-9600
At the corner of Madison Avenue and East 45th Street—the central stomping grounds for real-life Don Drapers of yore—step into The Roosevelt Hotel, the site of Sal Romano's clandestine date with a Belle Jolie representative and Don's temporary bachelor pad after Betty, his wife, kicked him out of the house in season two. Pass through the sumptuous lobby of this classic New York hotel on the way to the Madison Club Lounge, whose mahogany walls, stained-glass windows and leather chairs look as if they were fashioned by a Mad Men set designer. After quaffing a scotch or two, head up to Mad46—The Roosevelt's sleek rooftop lounge—to get your fill of contemporary New York cool while gazing out over the cityscape from 19 floors up.

234 W. 44th St., 212-221-8440
For a pre- or post-theater meal in a historic New York setting, head over to Sardi's, a landmark restaurant renowned for the celebrity caricatures that swathe its dining room walls. Once a hotbed of Broadway glamour—hosting glitzy Tony Awards parties and serving as the go-to hangout for prominent members of the Broadway community—Sardi's is now more of a draw for hungry tourists than for the Broadway glitterati. Nevertheless, this New York institution continues to serve up solid Italian and American fare and, after more than 80 years, remains one of the most popular Theatre District restaurants. Mad Men fans will recognize Sardi's as the site where Don and Bobbie Barrett celebrated the sale of TV pilot Grin and Barrett with drinks, which led to Don's car crash en route to a tryst at Bobbie's Long Island home.

The Grand Central Oyster Bar & Restaurant
89 E. 42nd St., Lower Concourse, 212-490-6650
If you fancy yourself a "fan of the mollusk," as Roger Sterling puts it, pull up a stool at the counter or a chair at a red-and-white-checkered table under the vaulted tiled ceiling of The Grand Central Oyster Bar & Restaurant. This magnificent subterranean space, located in Grand Central Terminal, possesses enough classic charm to fool diners into expecting Don Draper to walk in right off the train from Ossining. For nearly 100 years, The Oyster Bar has served tourists, suburban commuters and Midtown suits their fill of fresh seafood—including favorites such as clam chowder, lobster and, of course, an impressive assortment of freshly shucked oysters. (Just don't overdo it on the drinks; this is the spot where Roger and Don shared a few too many lunchtime cocktails, causing Roger to lose his oysters at the feet of Richard Nixon's campaign staffers back at the office.)

P.J. Clarke's
915 Third Ave., 212-317-1616
Established in 1884, P.J. Clarke's was vintage even to the Sterling Cooper crowd when, in season one, they drank and danced the twist at this famous New York watering hole in celebration of Peggy's copy for the Belle Jolie ad campaign. Inside, you'll see that time has stood still since then. After-work patrons still pack the bar area to enjoy frosty mugs of beer and hear Frank Sinatra on the jukebox, while the dining room serves up mouthwatering comfort food (including, according to Nat King Cole, "the Cadillac of burgers") to locals, tourists and a laundry list of celebrities.

Bloomingdale's. Photo: Julienne Schaer

1000 Third Ave., 212-705-2000
One of New York's premiere shopping institutions, Bloomingdale's has been in its current Midtown East location since 1886, sending stylish ladies home with Little Brown Bags full of luxury cosmetics, apparel and home goods. Though Bloomingdale's boasts a sprawling selection of high-end classic and contemporary menswear as well, with unexpected bargains around every corner, Pete Campbell was quite embarrassed to be caught by an old friend in the returns line here exchanging a duplicate wedding gift—a ceramic Chip ‘n’ Dipduring his lunch break.

The Waldorf=Astoria
301 Park Ave., 212-355-3000
The Waldorf=Astoria has been a revolving door for the rich and famous for over a century. This distinguished Park Avenue hotel, founded by Astor cousins William Waldorf and John Jacob, is the accommodation of choice for New York City's most prominent visitors—including every US president since Herbert Hoover, United Nations ambassadors and foreign royalty—not to mention the onetime residence of Marilyn Monroe, Paris Hilton and, more recently, Brad Pitt and Angelina Jolie. In Mad Men, hotelier Conrad Hilton (whose Hilton hotel empire, incidentally, owns and operates The Waldorf=Astoria) added his name to this illustrious list, meeting with Don in his suite and raving about the food ("best kitchen in the world—got a salad named after it," he says). To sample some of the food for yourself, including the signature Waldorf salad, feast on an haute meal at Bull and Bear Steakhouse, or tuck into one of the City's most indulgent brunches at Peacock Alley.

'21' Club
21 W. 52nd St., 212-582-7200
Though it has never actually been featured on Mad Men, '21' Club could easily serve as a stand-in for any of the swanky, nameless restaurants where Don, Betty and the Sterling Cooper ad men wine and dine. Opened as a Prohibition-era speakeasy—and narrowly surviving numerous police raids, thanks to a secret wine cellar and an intricate, lever-operated system for the disposal of contraband liquor—'21' Club, in its current Midtown location for the last 80 years, has always been synonymous with New York society. Appearing in countless films and television shows, '21' Club has long been a favorite hangout for celebrities, from the likes of Groucho Marx, Katharine Hepburn, Ernest Hemingway and Frank Sinatra to nearly every US president since Franklin Delano Roosevelt. Even today, '21' maintains a dignified ambience, as one of the few remaining restaurants in the City with a strictly enforced dress code, and continues to serve classic American fare to a distinguished crowd.

Paul Stuart
Madison Avenue and East 45th Street, 212-682-0320
To outfit yourself in signature Mad Men couture, look no further than Paul Stuart. Generations of Don Drapers and Roger Sterlings have flocked to the clothier, a veritable Madison Avenue institution, for all types of classy menswear—from narrow-cut suits (fully equipped with pocket squares, naturally) and dress shirts to tie clips, cuff links, collar bars and all other accoutrements of a high-powered business ensemble. After more than 70 years, this world-renowned retailer continues to dress stylish gentlemen, from politicians and celebrities to Wall Street tycoons and, of course, Madison Avenue advertising execs, with tailored attire for all occasions.

Chisholm Gallery
325 W. 16th St., 212-243-8834
Advertising may be an art to Don Draper, but at the Chisholm Gallery in Chelsea, advertisements literally are the artwork. Owner Gail Chisholm maintains a rotating collection of roughly 3,000 original vintage advertisements—dating from the 1890s to the early 1970s—whose inspired concepts and exquisite imagery would impress even the most discerning clients. Stocked with fascinating ads for a variety of brands—ranging from airlines and tourism boards to beers, wines and even wartime propaganda—the Chisholm Gallery functions as an intriguing testament to the rich history of the advertising industry.