On TV’s Mad Men, Don Draper, Sterling Cooper Advertising Agency’s creative director, and his family make their unhappy home in the Chilmark neighborhood of Ossining. The year is 1963. Mad Men series creator Matthew Weiner told Westchester Magazine he chose Ossining for “the same reason John Cheever did—because there’s a prison there.”But Sing Sing isn’t the only Westchester locale playing a supporting role on the AMC award-winning drama. Check out the following spots to recreate the Drapers’ Westchester experience (without the depression and adultery, of course) before the third-season finale on November 10.
1) Ossining Train Station
1 Main St, Ossining
Until the last five minutes of the show’s first episode, Don Draper appears to be a sweet-talking Manhattan adman with a Greenwich Village bohemian girlfriend. It is when Draper pulls into the Ossining train station in the series premiere that the audience starts to realize that he is leading a double life, shuttling between his cosmopolitan affair and his unsuspecting wife and kids in the ’burbs.
Be Like Don Draper: Nix the affair, but take a ride on the railroad. The New York Central Railroad Draper rode from Ossining is now Metro-North’s Hudson Line, which will take you into Grand Central Station. (A monthly pass cost $33.96 in the ’60s; it’ll run you $243 today for the same ride into Midtown.) Draper likely smoked Marlboros and drank whiskey on the commute, but lighting up was banned on Metro-North
trains in 1988. And although you’re still allowed to drink alcohol on Metro-North, the Hudson line lacks the bar car—to buy a drink on board you’ll need to take the New Haven Line.
2) Antiquing in Tarrytown
While attempting to furnish baby No. 3’s room, Don’s wife, Betty, declares, “We should really spend the day in Tarrytown. It would be so easy.” Son Bobby argues, “Those stores smell bad.” His dad won’t have it. “We’re going to Tarrytown,” he says, “and you’re going to stare at an antique chair for so long, the buttons are going to seem interesting. And then we’ll go to Carvel.”
Be Like Don Draper: Tarrytown is still the antiquing hub of Westchester. But what the Drapers considered contemporary in 1963, many Tarrytown antiques shops today carry as retro pieces. Indeed, you can dress your house like the Drapers’. Check out Belkind Bigi for the best mid-century modern furniture. And for that famous soft-serve cone, Westchester is home to dozens of Carvels—though their numbers may be dwindling—including one in Briarcliff Manor, practically in Don Draper’s backyard.
21 Main St, Tarrytown
1874 Pleasantville Rd, Briarcliff Manor
3) Rockefeller Estate
When an acquaintance who flirts with Betty Draper tells her he was just in Pocantico Hills for Governor Nelson Rockefeller and Margaretta “Happy” Murphy’s wedding, Betty voices her disapproval of the union. At the time, the marriage was considered quite the scandal: Happy had divorced only a month earlier and she was 18 years younger than
Be Like Don Draper: While marrying Happy may have ended Nelson’s chances of becoming president, Happy helped Nelson create a sculpture garden at Kykuit, the Rockefeller estate, which includes works by Pablo Picasso, Alexander Calder, and Henry Moore. Take a tour of the 40-room Kykuit any day of the week (except Tuesday) and make sure to check out the Italian garden and the Adam and Eve fountain area on the premises.
381 N Broadway, Sleepy Hollow
4) Brookside School
Troubled child Sally Draper attends Brookside Elementary School in Ossining and, during a parent-teacher conference to discuss Sally’s troubled behavior, Don lusts after her free-spirited teacher.
Be Like Don Draper: Move to Ossining and send your kids to Brookside. Little Sally’s class is lily-white (and, in fact, even more than a decade later, in 1974, only 2.4 percent of Brookside students were black). A 1969 New York State study named Ossining one of the 54 most segregated districts in New York. Race riots broke out at Ossining High School between 1968 and 1974, the year the school board announced its integration plan. The plan divided students into four newly carved, demographically and socioeconomically balanced elementary school districts. As a result, today Ossining is one of Westchester’s most racially integrated school districts.
Brookside Elementary School
30 Ryder Rd, Ossining
5) Sing Sing Prison
And then, of course, there’s the reason Weiner chose to set his show here. While Betty is attempting idle country-club chatter at a Memorial Day party, another woman turns the conversation to the Rosenberg execution at Sing Sing and says, “I keep having a dream that there’s a power failure and the gates open.” Betty, in an example of her refusal to face the dark reality of her life, says, “Let’s change the subject.”
Be Like Don Draper: While the Drapers steered clear of Sing Sing, today you can go to the Sing Sing exhibit at the Joseph G. Caputo Community Center and see a replica of the electric chair used to execute Julius and Ethel Rosenberg (it ceased operation in 1963). But don’t expect an Alcatraz experience—though a full-scale museum has long been talked about, Sing Sing is still a maximum-security prison that houses 1,700 prisoners, prohibiting tour groups.
Sing Sing Prison Exhibit
Joseph G. Caputo Community Center
95 Broadway, Ossining
Diana Scholl is a New York City-based journalist who was born and raised in Ossining and has watched every episode of Mad Men.