The Upstate Supercommuters Moving Downstate

In May 2022, two years into the pandemic, Sunny Jenkins found herself captivated by what she glimpsed in the background of a Zoom call — a grand staircase, a fireplace, and a farmhouse dining table. The person she was talking to lived in the Hudson Valley, and Jenkins, who was living in Laurel Canyon with her husband and young daughter, realized that she could move there, too. Her husband was fully remote, and she was hybrid (and her own boss, as the founder of a PR firm with clients in New York and L.A.). Several months later, they’d sold their L.A. home and moved into a dreamy, Georgian-style four-bedroom in Chatham, about two and a half hours north of midtown Manhattan. The house was fully renovated and sat on two landscaped acres with a stone terrace and a restored 2,000-square-foot barn. In short, the perfect place for two self-employed people to work from home.

But Jenkins was soon going into the city as much as, if not more, than she was working from home — as in-person meetings and events picked up, she increasingly felt the need to attend. “I was definitely optimistic about moving up there, but I don’t think I totally understood the landscape,” she says. What had seemed like “a pretty quick Amtrak ride” was in fact almost two hours each way, on top of a 25-minute drive to the train station in Hudson. “Door to door, the whole thing was taking three hours,” she says. Sometimes she’d stay over at the office, a mixed-use loft in Nomad, but it was hard to do that regularly with a young daughter, so occasionally she’d end up doing the whole six-hour haul in one day. Still, Jenkins was adamant about not moving to the city. “I really love the Hudson Valley. I love the lifestyle. I loved the house,” she says. So she and her family relocated to a rental in Rhinebeck, which cut nearly an hour off the round-trip commute. “I just couldn’t handle the yo-yoing,” she says. “We needed to be further south.”

Call it the dilemma of the accidental supercommuter. During the early years of COVID, buying a place two or three hours from Manhattan seemed not only feasible but, in many cases, sensible. Instead of cramming two desks and a Peloton into an 800-square-foot apartment, you could have a spacious farmhouse, a yard, and a spare bedroom. Even at COVID-inflated prices, a million dollars bought a lot more in Red Hook, New York, than it did in its Brooklyn counterpart. Stephanie Diamond, the founder of the Listings Project, a housing-and-job-listings community, who lives upstate herself, witnessed the surge of interest in real time: “Our ‘seeking living space’ category was the fullest it had ever been.” She’s since seen many of those who moved to the region leave: Some came to realize that chopping wood and maintaining 100-year-old houses was not for them, while others decided to embrace the freedom of being fully remote and move to another state or country entirely. But there are still many more who fell hard for upstate life, and now that employers are increasingly mandating that workers return to the office, they’re doing whatever they can to stay. For many, that means moving a little bit closer to the city, or at least closer to a train station.

Photo: Sotheby’s International Realty

When Paige Kendig, a senior producer on The Late Show With Stephen Colbert, moved from Brooklyn to Chatham at the start of the pandemic, she knew, unlike Hasselbring, that the commute would be brutal and that eventually she would have to go back to the office. But she fell in love with small-town life. When the three-hour drive (four in bad traffic) proved too much, she and her boyfriend moved south, buying a cabin in Staatsburg, a small town situated between the Amtrak station in Rhinebeck and the Metro-North stop in Poughkeepsie. She’s glad they didn’t have to give up some of their favorite things about living upstate. “It feels very remote — we have a vegetable garden, a dog, we chop down trees — but it’s an hour-and-a-half-long train ride to work,” she says.(The only downside, she tells me, is that, having gone about as far south in the Hudson Valley as they could, they’re now kind of a schlep from a lot of their friends up north; Hudson is a 40-minute drive.) Most people she knows who moved upstate during COVID have made some kind of adjustment to keep the country idyll going — moving closer to the train, keeping an apartment in the city where they can stay a few nights a week, changing careers, even turning down promotions that would mean going back to the office every day. “I don’t know anyone who’s moved back full-time yet,” she says.

Jared Vengrin, a real-estate agent at Corcoran, says that he’s been having a lot of conversations in this vein with clients — people looking to move from places like Stone Ridge and Accord to Northern Dutchess County. He also runs a motel in Red Hook that served as a staging ground for house hunters during the pandemic, and he observed firsthand that while some were canny about buying within commuting distance, a lot of buyers were tempted by houses that were significantly further out, where they could get more for their money, especially in the heady days of fully remote work and the real-estate frenzy that followed, with buyers snapping up houses as soon as they hit the market. “Now many are selling,” he says. At the same time, “there’s a lot of activity around any listing in Hudson or Rhinebeck — places that have good proximity to Amtrak.” (The Rhinecliff train station is, I’ve been told, a madhouse on weekdays — “if you miss the first train out, you’re screwed,” one commuter told me. “And people park in the most ridiculous ways — they’ll pull up onto boulders if all the parking spaces are taken.) Vengrin’s family was, he added, doing a similar shift — moving from northern Red Hook, which is more rural and further away, to the village of Red Hook and taking back their Brooklyn apartment from renters so he can come into the city three days a week for his other job at a recruiting firm.

Photo: Anatole House

Long commutes might be the biggest factor, but some people have also left far-out, secluded spots for towns and villages. The things that are appealing in a second home aren’t always what people want from a place they’re living in full time. It turns out a lot of former New Yorkers really like walkable towns where they can go around the corner for a cup of coffee and run into other people, and they especially like not having to drive a long time for basic necessities. MJ Collum, a real-estate agent at Anatole House, an upstate brokerage, says, “I’ve seen a lot of people who bought in really remote areas moving to be closer to community — selling their houses and moving to a village.” This is what prompted Summer Wick’s recent move to Kingston. In 2021, she moved with her husband and daughter from Portland, Oregon, to Tillson, a small hamlet 20 minutes outside of Kingston. They bought a 1939 farmhouse and renovated it to a shelter-mag-worthy state. At first, it wasn’t a huge deal that the house was somewhat isolated. But her daughter’s school is in Kingston, as is her swim team. And on weekends, Wick would have to drive all around the Hudson Valley to different markets to sell her candles. “The house was beautiful, but we were driving a ton,” she says. So this August, they sold it and bought a place in Kingston instead. An added benefit: Wick’s daughter, a teenager, can get around by herself, as she prefers. But they had a lot of competition. Even now, when the market is less frantic, they ended up in a bidding war over the house they did buy, a 1900s fixer-upper.

After years of toggling between a house in Kerhonksen and a place in the city, Alex Kahn and her husband made a similar move. They’d closed on their Kerhonkson house the week the world shut down, and what was supposed to be a weekend project while they lived in Brooklyn became their home base, while Brooklyn became the fun getaway where they kept a room in their old house share. “It was like the best of both worlds — I could go down and see people and come home and read by the fire,” she says. It worked with a dog, but after they had a baby, that kind of back and forth wasn’t possible anymore. They decided to stay upstate — she loves how calm it is, having a house and yard, and all the great restaurants and coffee shops that have opened since the pandemic. But Kerhonkson was just a little too far — it’s an hour to the Rhinecliff train station — so they moved to Kingston, which is just 20 minutes from the train. Moving there also meant they could run errands and do other activities without a long drive. While her social circle is still largely in Brooklyn, Kahn has no intention of moving back.

Still, shaving 45 minutes off a commute is a rough compromise. Even the closest Hudson Valley towns require hours on the train. One communications professional I spoke with who moved during the pandemic to Rhinebeck, close to where she grew up, says that she’s able to swing commuting to the Upper West Side two or three days a week only because her husband is fully remote and handles kid duties on those days, when she’s gone from around 7 a.m. until 8 p.m. — a full 13 hours. And even a relatively minor change to the train schedule can wreak havoc on the carefully calibrated planning that makes long-distance commuting possible. Several people told me how thrown off they were when Amtrak pushed the 6:36 morning train up to 6:09. Then there’s the specter of a five-day office return looming over the delicate balance that everyone is striving to maintain. One woman I talked with who moved to Rhinebeck in 2022 is currently required to be in her Hudson Yards office three days a week, but it’s going up to five in May. She’s optimistic about making it work — she’s been renting an under-market apartment from a friend, she doesn’t have kids whose schedules she has to coordinate with her husband (although they do have a dog), and she’s grown to like some things about commuting; she’s reading more books, for one. Even so, she admits, the whole arrangement feels precarious. “I’m constantly waiting for the other shoe to drop.”