Gary Bassett moved to Rhinebeck, N.Y., in 1993, after being transferred by his employer, IBM, from Wisconsin to a plant in nearby Kingston. The village of about 2,600 residents in the Hudson Valley reminded him and his wife, Brenda Bassett, of their small hometown in central Pennsylvania, and they felt an immediate kinship with the place.
They’ve now lived there for nearly 30 years, which would make you an old-timer in most places. But Rhinebeck has a 300-plus-year history, and a long memory.
The village of Rhinebeck — which sits inside the town of Rhinebeck, like “the hole within the doughnut,” Mr. Bassett said — is home to one of the oldest operating inns in the country, Beekman Arms & Delamater Inn. And houses there are known not by the people who live in them today, but by those who lived in them a century ago. Both town and village are within the Hudson River Historic District, which includes more than 40 riverfront estates and, at 32 square miles, is one of the largest historic districts in the country.
“I know people who have lived their whole lives here,” said Mr. Bassett, who is mayor of the village. “The residents of Rhinebeck take a lot of pride. We work hard to keep that historic preservation alive.”
At the same time, he added, “there’s that transition of new people coming in. The area is changing.”
Locals cite the wedding of Chelsea Clinton, in 2010, at a village estate once owned by John Jacob Astor IV, as a turning point. Rhinebeck went from what Catherine A. Mondello, a local realtor, called “a laid-back country town, a Mayberry,” to a popular destination for day-trippers up from New York City, as well as a community where retirees and younger urbanites choose to relocate.
“Since then, we’ve just seen the trend moving up,” Ms. Mondello, the owner and principal broker of Mondello Upstate Properties, said. “The village is bustling.”
Vanessa Bertozzi and her husband, Mickey Duzyj, are two recent transplants. The couple had been living in Red Hook, Brooklyn, where she worked for Etsy and he pursued a career as a filmmaker. But their apartment felt cramped after their second child was born, and Etsy, which has an office in Hudson, N.Y., offered Ms. Bertozzi the opportunity to move upstate.
The couple chose Rhinebeck because the public schools are good and because it gave their two sons a version of the small-town childhood that Ms. Bertozzi experienced in New England. In 2017, the couple paid $430,000 for a four-bedroom, two-and-a-half-bathroom home in a newer subdivision in the village. That looks like a bargain now, as Rhinebeck, like many upstate towns, has experienced soaring housing prices during the pandemic.
“It’s not a beautiful home, but because we got a good price, we’ve been able to redo stuff,” Ms. Bertozzi said. “We redid the deck and the front porch to give it more curb appeal. That’s been fun as first-time homeowners.”
Ms. Bertozzi has had little trouble adapting to life outside the city. Rhinebeck Village has ample cultural amenities, including a bookstore, a movie theater and two public libraries, while the town offers wide-open farmland, winding country roads and the Hudson River, which runs along its western border.
“Everyone takes such wonderful care of their gardens. There are tree-lined streets here,” Ms. Bertozzi said. “It’s a place that’s really proud of its beauty. It’s just a very attractive village.”
What You’ll Find
The village of Rhinebeck, at the center of the town, is small but vibrant and lively, especially on weekends. Packed into its 1.53 square miles are nearly two dozen restaurants; the well-known bakery Bread Alone; a high-end spa, Mirbeau Inn & Spa; several art galleries and clothing shops; and a candy store, Samuel’s Sweet Shop, co-owned by the actors Paul Rudd and Jeffery Dean Morgan. On a recent visit, there was hardly a vacant storefront.
The Beekman Arms, with its white-brick facade, black shutters and landscaped front yard, stands regally on a prominent corner as you enter the village. On the streets behind the business district are beautifully preserved old houses. There is a noticeable sophistication and wealth to Rhinebeck that you don’t find in some neighboring towns — it’s a quaint upstate village polished to a high shine.
Lydia Slaby, a writer and village trustee who moved to the area in 2018, called the village “the center of gravity” for the more rural town and surrounding countryside. (The traffic certainly makes it feel like a crossroads.) Ms. Slaby followed her sister, who had bought a 17-acre farm in the town, and her aging parents, who moved to a cottage on the property. She and her husband, Michael Slaby, an executive at a nonprofit, had been living in Chicago and first visited Rhinebeck on a snowy day at Christmastime, in 2011.
“I thought it was beautiful up here. It’s like wandering around in a painting — which makes sense, because there was that whole painting school,” Ms. Slaby said, referring to the Hudson River School movement. “Everyone was saying ‘hi’ to each other. This is an actual community.”
The couple rented an 1883 Victorian on half an acre,…