Pine Plains Is a Beautiful Place to Settle Down in the Hudson Valley

Pine Plains is a bustling Hudson Valley town that delights with everything life in the country has to offer.

In 2021, Alex Athanasiadis—like many others worn down by the pandemic in New York City—needed an escape. Looking for a rural spot to settle down and open his dream interior design store, he scoped out nearly every small town in the Hudson Valley. When he visited the Dutchess County town of Pine Plains, he felt an immediate connection.

“Pine Plains has so much beauty—the natural beauty, the buildings, the farms—I was instantly attracted. Then I met the people and loved it even more,” he says. He opened his design shop Demeter Home on East Church Street in 2021 and last year, he and his husband bought a house.

The town was first formed by the 1706 Little Nine Partners Patent, a document that assigned property ownership of the land we now know as Pine Plains, Milan, and North East to different patroons. According to town records, the area was “somewhat of a backwater” at the time.

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In 1823, Pine Plains was formally established, taking its name from an early description that noted the area’s abundance of pine trees blanketing the valley. Despite a brief period in the late 1800s when it was overrun with rail travel, the quiet area has always been supported by agriculture.

The Culture

At the center of town, you’ll find The Stissing Center, a hub for chamber music, jazz, and theater, and the cultural pillar of Pine Plains. “We are working hard to position The Stissing Center as the preeminent venue for world-class arts and culture in the region and make it accessible to the part of America [outside of cities] where people don’t necessarily believe great art exists,” says executive director Brett Bernardini. (Caña Dulce y Caña Brava, a Mexican music group, will perform on October 21.)

The Stissing Center
The Stissing Center. Courtesy of Dutchess Tourism.

This year, the community has been honoring its bicentennial with a variety of events. “The bicentennial has highlighted what a vibrant community Pine Plains has always been. There is a renewed sense of excitement around the town and a desire to make it the best version of itself,” says Athanasiadis. This month’s celebrations include Ag Day and fireworks on October 7.

Family Life

Pine Plains is a small community of 2,200 residents, and because of its increasing popularity, there are few houses for sale. At press time, there were nine homes on the market with a median price of $955,000, according to Zillow.

School District. Stissing Mountain Junior/Senior High School has 505 students in grades 6–12. The Pine Plains Free Library offers an array of family-friendly programming throughout the year, including story time on Saturday mornings and a make-and-play workshop on Thursday afternoons.

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On the Town

In Pine Plains’ quaint village, you’ll find a diverse mix of high-end restaurants and casual eateries. The Stissing House is led by critically acclaimed chef Clare de Boer, who serves up seasonal American meals; authentic French cuisine shines at Champetre; and Lia’s Mountain View cooks up homemade Italian. For quick bites head to Spud Shack or Moose on the Loose.

Stissing House restaurant
Stissing House restaurant. Courtesy of Dutchess Tourism.

The town boasts two outstanding home design stores, Demeter Home and Hammertown Barn. There’s also the Brown Bag Boutique for secondhand clothing, books, and more, and Hugs & Kisses for floral arrangements.

The rural location makes Pine Plains ideal for enjoying outdoor activities. Stissing Mountain has a challenging 1.8-mile hiking trail with a climbable fire tower at the summit. At the base are water sports opportunities—Twin Island Lake, Stissing Pond, and Thompson Pond are open for paddle-boating and fishing year-round. Just south of town is the Buttercup Farm Audubon Sanctuary, perfect for birdwatching in any season.

The fire tower at Stissing Mountain.
The fire tower at Stissing Mountain. Photo by @9th_letter.

Both Bernardini and Athanasiadis, who are newer arrivals to the Pine Plains area, share that their experiences moving to the small town have been nothing but positive. “Our town is a snapshot of rural America. You’re not going to come out here and find rocking nightlife, but what you will find are authentic people who show up exactly as they are, and proud of it,” says Bernardini.

To find a real estate agent in Pine Plains or any Hudson Valley town check out near-me.hvmag.com/realtors.

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Related: Pawling Is a Small Town With Charm in Southern Dutchess County

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