Westchester history and little known facts

Westchester History

Tarrytown is home to a bit of Westchester history, including the Tarrytown Lighthouse and Tarrytown House.

From Bedford Hills to Bronxville and Pelham to Port Chester, DealChicken has spent a lot of time hunting and pecking for the best daily deals around the towns and villages that compirse affluent Westchester County, NY. So it’s no surprise he’s come across a good deal of fascinating Westchester history. Here’s a bit of local trivia that even your favorite fine-feathered know-it-all didn’t know until recently.

Boasting the 2nd highest median household income of any neighborhood in America according to CNN Money, Scarsdale is one of Westchester’s most famous principalities—but it’s also known its share of scandal. Its wartime history formed the basis for James Fenimore Cooper's novel, The Spy, written while the author lived at the Angevine Farm in the present-day Heathcote section of town.

Although the TV show, Seinfeld, was often critiqued for being too “New Yorkey”, they often featured stories involving the ritzy suburbs of Westchester. Witness one episode, wherein Kramer is accidentally handed a Tony Award for the fictional musical "Scarsdale Surprise", purportedly based on the Scarsdale diet doctor’s 1980 murder.

One of only a handful of so-called “sparkplug lighthouses” in the U.S. that is still open for tours, Tarrytown Lighthouse was built from a kit and installed in Hudson River in 1883. Inactive since 1961, its 60-foot round tower sports a lantern and double gallery, including 4-stories of keeper's quarters, mounted on cast iron caisson. The lighthouse is accessible from shore by a footbridge.

Most everyone knows that Westchester has been home to the rich and famous since long before the term “reverse commute” became common parlance; but most folks would be surprised to learn that a tour of Westchesters’s several historic homes—Kykuit (a.k.a. The Rockefeller Estate), Van Cortlandt Manor, Tarrytown House and Lyndhurst Castle, to name a few—will also double as an art buff’s dream tour. Along with expensive crystal, furniture and knicknacks, these architecturally-mesmerizing structures shelter some of the most impressive private collections not just in Westchester history, but of anywhere in the U.S.


Ossining, one of the more difficult Westchester towns to pronounce, was nearly named something far easier to say. In 1881, the town considered changing its name to "Garfield Plains" to honor the recently assassinated President of the United States, James Garfield, but dropped the idea after the much larger city of White Plains in southern Westchester County objected. In 1901, to prevent confusion of goods made in the village with Sing Sing prison-made items, local officials had the village name changed to Ossining as well.

Rye’s Playland is the first planned amusement park in America. Located on the shores of the Long Island Sound, the park features 50 rides for adults and kiddies (in Kiddyland), plus miniature golf, midway amusements and live entertainment at the height of the summer season. Playland’s boardwalk is open 365 days a year, and even if you’ve never visited, their quarter-mile pier may look familiar. Playland’s boardwalk provided the backdrop for Tom Hank’s big “I want to be big” scene in the 1988 film, Big. Alas, the Zoltar machine that grants his "big" wish was just a show biz prop—no such fortune teller exists.

Famed author and playwright Lillian Hellman lived at Pleasantville’s  Hardscrabble Farm during the 1940s and ’50s. Although Hellman’s relationship with infamous writer Dashiell Hammett is common knowledge, the fact that the not-so-glamorous scribbler was the inspiration for the character of Nora Charles from the Thin Man series of movies is apt to raise eyebrows.

Walter’s Famous Hot Dog Stand in Mamaroneck, in operation since 1919, serves just one item (guess what that is!). However, the pagoda-shaped stand really makes that short menu count: their weiners, split down the middle and grilled in a secret sauce (a homemade mustard-and-relish mix), were rated the Best Hot Dog in the Country by Gourmet magazine in 2001!

Ironically, although Facebook creator Mark Zuckerberg was born in the college town of White Plains, he opted to matriculate at Harvard University instead of one of the eight closer-to-home alternatives.

Valhalla, NY may be named for the Norse kingdom of heaven, but its Kensico Cemetery could earn the title of “graveyard to the stars”: Kensico is the resting place of numerous famous people, including actress Anne Bancroft, author Ayn Rand, baseball great Lou Gehrig, Salvation Army founder William Booth, and actress Billie Burke, who played Glinda the Good Witch in 1939’s The Wizard of Oz.

Are you already a Westchester history whiz? Check out our Ithaca page.