The countdown to the season premiere for Mad Men has begun. We know that Betty has left Don for Henry, and Sterling Cooper is in the process of reinventing itself.  The big question lingers … where and with whom will Don Draper land?

Throughout the series, Westchester County has played a role, with Ossining the home town of the Draper family. Those who live in the town are thrilled that Mad Men has given Ossining a new identity that now overrides being home to Sing Sing. 

Westchester was also prevalent in another iconic 1960s program, The Dick Van Dyke Show. Rob and Laura Petrie are residents of New Rochelle in the series. Like Don Draper, Rob Petrie commuted to the city while their respective wives were stay-at-home moms wearing the uniform Capri pants and bouffant hairdo.

Why Westchester and not say, Long Island or New Jersey as the backdrop for 1960s suburban life? Some would say the underlying sophistication of both programs – the Petrie’s home was contemporary with the infamous step-down living room, and both characters worked in glamorous and creative professions – required equally urbane towns in which to live out their respective dysfunctional or comedic storylines. It would appear that Ossining and New Rochelle were the ideal locations to come home to from the cigarette smoking, three-martini lunches in the City that defined the era.

Where in Westchester do today’s modern-day Mad Men or comedy writers live?

Meanwhile, as the Mad Men theme song has become iconic – some fans have the song as their ringtone — this home for sale in Ossining with a recording studio is quaintly relevant to Mad Men-mania. This The Wall Street Journal home tour features Rob Thomas recording with music Producer Hal Winer.