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Millerton, N.Y.: Unspoiled Beauty With a New Youthful Energy

In 1998, Stephen Leven and his business partner, David Elwell, bought a farm in the upstate village of Millerton, N.Y., turning the old carriage house on the property into a roastery for their coffee company, Irving Farm New York. In 2003, the men opened a cafe on the village’s Main Street (their other seven locations are in New York City).

For years, Mr. Leven and Mr. Elwell, both city dwellers, alternated weekends on the farm. In 2014, Mr. Leven built a house nearby, but remained a weekender. And things might have continued that way, if not for Covid-19.

Living the country life full-time during the pandemic, Mr. Leven saw the community in a wondrous new light. “Just as the city was locking down, people were out and about here,” he said. “We were outside a lot. We were eating food from farm stands. The quality of life was very high. We wanted this to be the way we lived.”

So last fall, Mr. Leven, 53, and his wife, Mira Trezza, 46, who have one son, Sasha, 9, sold their brownstone in Bedford-Stuyvesant, Brooklyn, and made their weekend home their principal residence. Even the cold winter hasn’t made them second-guess the move. “We sled when it snows, whereas before, if the weather was cold, we’d stay inside,” Mr. Leven said. “We just can’t get enough.”

The Dutchess County village has much to recommend it. There’s the Harlem Valley Rail Trail, a beacon for bikers; a walkable downtown with antiques shops, restaurants and a bookstore; historic buildings including a circa-1850 schoolhouse and a general store from 1919; and something that no other nearby town has: a movie theater.

For years, such cultural amenities, combined with Millerton’s affordability and casual pace, attracted New Yorkers like Allan Ripp, a public-relations professional who bought a second home there with his wife Sarah, 64, in 1989. In Millerton, Mr. Ripp, 67, found “a little village, time-warp 1950, with immediate access to incredible countryside, natural beauty, farms.”

The unspoiled beauty remains, but Millerton is no longer stuck in time. Over the past decade, Brooklynites have flocked to Hudson Valley communities, including Millerton, bringing a youthful energy and spawning businesses that cater to their tastes. The Oakhurst Diner, formerly a greasy spoon, serves pho and Beyond Meat burgers. Saperstein’s, a five-and-dime that for decades sold everything from work boots to baby clothes, is now Westerlind, a high-end outdoor apparel and home boutique that opened last May.

A hundred miles north of New York City, Millerton had previously seemed too far away to be a commuter town. But the rise of working from home during the pandemic has created new living possibilities and, at least for some, reversed the traditional weekenders’ routine.

“There’s this shift that you go to the city for the weekend and live upstate, as opposed to going upstate for the weekend,” said Westerlind’s owner, Andrea Westerlind, 39. “There’s really very little need to be in the city.”

Ms. Westerlind and her husband spent last summer looking for a home in Millerton. They offered the asking price of $300,000 for a turn-of-the-last-century home with a large garden within walking distance of her store, but were outbid, she said. The couple and a friend ended up buying a five-acre property with three houses in Ashley Falls, Mass., about 20 minutes away.

With just 0.62 square miles and about 900 residents, Millerton is blink-and-you-miss-it tiny. It is part of the town of North East, N.Y., population around 3,000. Millerton has its own mayor, while North East has a town supervisor. Each municipality has its own highway department, and Millerton has a small police force. There are separate zoning boards.

The median household income in Millerton is $36,176, according to the most recent census data. The racial makeup is 93 percent white, 2 percent Black, 1 percent Asian and 4 percent Hispanic. Residents tend to fall into three camps: locals who grew up in the area, transplants and city people with weekend homes.

With the Connecticut border a mile to the east and Massachusetts less than 20 miles north, the village has the feel of a crossroads, especially as Route 44 runs through its center. Residents of Connecticut towns like Salisbury and Sharon might drive to Millerton to dine out or shop at the weekend farmers’ market, while Millerton locals might head to the Berkshires to take in cultural events at Tanglewood, Mass MoCA or the Mahaiwe Performing Arts Center.

“Millerton was always a good business town,” said Lew Saperstein, who ran his family’s five-and-dime until he sold the building in 2018. He remembered assisting Meryl Streep, who lives in Salisbury, back when the actress was a young mother. “She used to shop in my store,” he said. “We’d be elbow to elbow, looking at these Mother Goose children’s shoes.”

With a limited supply of around 400 homes and considerable demand, Millerton’s housing market is, like most everywhere these days, white hot.

“If anything hits under $300,000 and it’s in decent condition, it’s gone,” said Arleen Shepley, associate broker at Elyse Harney Real Estate. “Lately, a lot of our clients are coming from Brooklyn.”

But property in Millerton has long been a relative bargain compared to that in Connecticut — and it remains so. In February 2021, the median list price for a single-family home in Millerton was $422,000, up 69 percent year over year, according to Realtor.com; the median sale price was $320,000.

Currently, there are two homes for sale in the village: a four-bedroom Cape Cod on just over an acre, listed for $370,000, and a two-bedroom, two-bathroom circa-1910 colonial, listed for $240,000. This time last year there were three times as many homes for sale in the village.

“The market is still hot, but there’s a lack of rentals and medium-priced homes,” said Brad Rebillard, the owner of Dutchess Country Realty, who has been selling real estate in the area since 1989. “There are more large vacant land parcels available for sale now.”

One property Mr. Rebillard currently has listed, outside the village in the town of North East, is a combination farm and specialty-income property with a kennel, a rental house and 33 acres to build on, listed for $1.9 million.

Historic homes in the center of the village, like the 3,700-square-foot Victorian that sold last fall for $577,000, attract the greatest interest. Less prized, especially by city transplants, are newer homes in developments just outside the village.

Rentals are scarce. “Even our locals are having a hard time finding affordable rentals,” Ms. Shepley said.

It’s hard to mark the tipping point — the opening of the rail trail? the menu revamp at the diner? — but Millerton has gradually become “cool.” In fact, Frommer’s Budget Travel magazine included it on a list of “10 Coolest Small Towns” back in 2007.

And when a sleepy rural village becomes a hip destination, it can cause tension between longtime residents and new arrivals. “In some communities, that tension can be destructive,” said Chris Kennan, the North East town supervisor. “Fortunately, in Millerton, while I’m sure it exists, it’s much less so.” Mr. Kennan cited his own personal history as evidence of community openness — he was a weekender who became a resident, got involved in local nonprofits and was elected to local office.

Millerton appears to exist in a sweet spot. It’s vibrant and on the upswing, but not yet overcrowded or overdeveloped. One source of mild resentment among locals, however, is a commercial mix that favors the visiting New Yorkers: While you can buy a $5.25 mocha at Irving Farm cafe or a $275 jumpsuit at Westerlind, there hasn’t been a supermarket in the village since the Grand Union closed four years ago.

A McDonald’s and a furniture store have also closed. Locals drive to the Walmart Supercenter in Hudson, a 60-mile round trip, and shop for groceries at the Freshtown in Amenia, N.Y., or in Rhinebeck or Poughkeepsie.

“But there’s still a shooting range in Millerton,” Mr. Ripp, the longtime weekender, said. “From our porch, we’ll still hear a shooting range. It’s not hillbilly, but it’s a reminder you’re not in Scarsdale or Brooklyn.”

Webutuck Central School District in Amenia, N.Y., which serves the village of Millerton, is the smallest district in Dutchess County. Around 200 students are enrolled at Webutuck High School. The Advanced Placement participation rate at the school is 27 percent. More than half of the students are economically disadvantaged and receive subsidized lunch.

City transplants often send their children to one of the many surrounding private schools, which include Millbrook, Hotchkiss, Salisbury and Berkshire. Mr. Leven enrolled his son at Indian Mountain School, a private junior boarding and day school in Lakeville, Conn. All are within a half-hour of Millerton. Other parents opt to send their children to Connecticut public schools in Lakeville or Sharon.

Millerton is a two-hour-plus drive to New York City, much of it on two-lane Route 44. But traffic remains as free-flowing as it was 30 years ago, Mr. Ripp said, and is nothing like the snarls leading to the Hamptons.

Wassaic station in Amenia, 11 miles away, is a commuter rail stop on Metro-North’s Harlem Line. A trip to Grand Central Terminal takes roughly three hours. Service has been temporarily reduced during the pandemic.

Millerton — named for Sidney Miller, who helped bring the railroad to the area — was founded in 1788, and the main business for many years was farming; there were local iron foundries as well, but they are long gone.

These days, the prominent surname in Millerton is Harney: In 1983, John Harney established Harney & Sons, a tea company headquartered there. His sons, Michael and Paul, now run the business. Paul is also an owner of the Oakhurst Diner. Their mother, Elyse Harney, owns the real estate agency in town.

With the exception of a few traditional milking farms and specialty farms with produce stands, working farms no longer exist in the village. Nevertheless, Millerton’s reputation as a farm community persists, especially among the city slickers. As Mr. Kennan, the North East town supervisor, joked: “A lot of people like to call their places farms when they have two horses out back.”

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