For decades, one of the most famous magazines in America told the world it lived in Pleasantville. It didn't, not exactly. The offices sat in Chappaqua, the next town over. The reason is so simple it's almost funny.
It Started Under a Secret Bar
DeWitt and Lila Wallace put out the first issue of Reader's Digest in February 1922. They worked out of a basement in Greenwich Village, under a speakeasy. That was a hidden bar, back when selling alcohol was against the law.
The magazine was tiny. The first issue ran 64 pages, and the cover promised "thirty-one articles each month from leading magazines." Each one was a shorter version of a story that ran somewhere else. That was the whole idea. Save people time, give them the best stuff.
The first issue even printed its own address. "No. 1 Minetta Lane, New York City." A copy cost 25 cents. A year cost three dollars.
A Garage and a Pony Shed
The Wallaces didn't stay in the city long. By September 1922 they were running the magazine out of a rented garage in Pleasantville, the village where they had gotten married. When they needed more room, they rented the pony shed next door too.
So yes. One of the biggest magazines of the century grew up in a garage and a shed. Every startup story in Silicon Valley owes Pleasantville a thank-you note.
Up the Road to Chappaqua
Reader's Digest got big fast. By 1938 there was an edition in Britain, its first outside the United States. The company needed a lot more room.
In 1939 the company moved into a new red-brick headquarters in Chappaqua. The building had a tall white tower on top, called a cupola. Four winged horses stood around it. In old Greek stories, a winged horse named Pegasus stood for inspiration, which is a pretty good mascot for a room full of writers.
That same year, architectural photographers Gottscho-Schleisner shot the brand-new building. Their photos are now in the Library of Congress. That's the 1939 picture in this post.
The Mail Still Said Pleasantville
Here's the twist. The company moved, but the mailing address didn't. Reader's Digest kept "Pleasantville, New York" on its mail. The reason, according to company histories, is that the Wallaces liked the sound of the name.
Fair enough. "Pleasantville" sounds like a place where good stories come from.
That address went on everything. In 1950 the company started Reader's Digest Condensed Books, shorter versions of popular novels sent to your house. A 1958 ad for the book club, printed on the back of Modern Screen magazine, had a mail-in shipping label. It reads "Reader's Digest Condensed Book Club, Pleasantville, New York." The company's official address was Reader's Digest Road, Pleasantville, NY 10570.
The Building Is Still There
Reader's Digest eventually left Chappaqua. By January 2011, the company was officially gone and the old headquarters sat nearly empty. The magazine is now based in Manhattan.
The building didn't go anywhere, though. The campus became Chappaqua Crossing. In 2018 the original 1939 building reopened as 64 apartments, a mix of market-rate and affordable homes. The cupola stayed, and photos from the 2018 opening still show the four winged horses on it.
So next time you drive past, look up at that cupola. It still sits on a building that spent decades pretending it was in Pleasantville.
Do you have an old Reader's Digest with the Pleasantville address on it? Show us on Instagram at @the914collective. And for more Westchester stories like this one, pick up Not Upstate Magazine at thenineonefour.com.
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