The Hudson River Valley is dotted with dozens of charming small towns.

Some are well-established communities already on weekenders’ radar, while others are lesser known but just as compelling. One such gem is Pine Plains in Dutchess County. Nestled between the towns of Millerton and Stanfordville and right on the border with Columbia County to the north, the few blocks that make up the town are packed with interesting shops, stellar restaurants, a theater that draws world-class entertainment, and of course, lots of wonderful houses.

Treat Your Tastebuds

Pine Plains has long been a destination for those who appreciate fine dining. For many years Stissing House, situated in an old 1782 Inn at the town’s main intersection, has been drawing diners from around the region. Now owned by chef Clare de Boer, one of the chefs behind Michelin-starred bistro King in Manhattan, it is hugely popular.

Just down the street is the excellent Champetre, owned by chef Michel Jean formerly of Provence in SOHO. Add to those haute cuisine hotspots the library/eatery Storybook Café, the popular Mexican restaurant El Guacamole, Tower Pizza, and the Spud Shack, and there’s an array of culinary choices to meet any taste.

Antiquing, Arts & Hiking, Oh My!

There are antique and design shops and other places to browse and buy. For those who love the arts, the Stissing Center offers theater, music and dance performances, hosting great classical artists like Eugenia Zukerman and The Brooklyn Rider Quartet, jazz legends like Winton Marsalis, and lots of Latin, folk, bluegrass, and other artists. The Stissing Center is itself beautifully restored and has some of the best acoustics in the area. And for nature lovers the town boasts the beautiful Stissing Lake and the local hiking spot Stissing Mountain.

Making Pine Plains Home

The town boasts a wide array of homes in a variety of styles and periods, from Victorian to craftsman, mid-century to classic 1970s ranches. And as the town’s popularity continues to grow, the homes that come on the market are increasingly in demand.

One such real estate opportunity is a turn of the twentieth-century home dripping with character centrally located at 7786 S Main Street. Once the town pharmacy and library, the home still contains many of the library shelves and the original apothecary drawers. With hardwood floors, beautiful moldings, a stunning mantle and original scrolled iron door hardware, four bedrooms plus a study and the original library, the spacious home is perfect for a buyer who wants to enjoy the local scene. Situated on a large lot, there is a porch perfect for parade-watching, gardens for flowers and vegetables, a large lawn, and a roomy barn with loft space that can be converted to office or studio space.

If you’re looking for a first or second home, a weekend getaway or a permanent address, or simply interested in spending a weekend in the country, be sure to explore the sweet and charming town of Pine Plains.

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