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10 Things To Love About Pine Plains

By Jamie Larson

Pine Plains seems to emerge out of nowhere. You’re driving through the woods between Dutchess County, N.Y. and Connecticut, and all of a sudden this handsome crossroads community pops up. Though small, Pine Plains has a surprising amount of reasons to visit, from the history to the food to the family farms. While the town may seem out of the way, it’s actually on the way to a lot of places, and a fabulous destination all on its own.

1. Hammertown
What can we say about Hammertown and its incomparable owner, Joan Osofsky, that we haven’t already waxed passionately about? The furnishings and housewares that fill Hammertown’s original location in Pine Plains have, in many ways, come to define the home decor aesthetic of the RI region: rustic yet styled, relaxed yet impeccably designed. Osofsky has literally written the book on this brand of style in Love Where You Live, and posts can’t-miss blogs and recipes on the store’s website. And as for those recipes, Osofsky has a new book, fittingly titled Love Where You Eat. Hammertown is more than a store, it’s a way of life.
3201 Rt. 199, (518) 398-7075

2. The Hudson Company
Refurbished reclaimed wood from dilapidated barns and other old or worn structures has become incredibly sought-after material in the interior design industry. It’s a real diamond in the rough and nobody’s better at sanding a beautiful floorboard out of a gnarled old beam than Pine Plains’ own Hudson Company. They’ve quickly become one of the industry’s biggest players in only a few years. Their success is due to the leadership of owner Jamie Hammel and a precise, efficient and quality-first facility outside of town. We recently wrote about how the company has been growing its profile exponentially, doing work for the Whitney, the High Line and countless other well-known institutions, restaurants and shops in NYC. But they’re also applying their supreme talents to homes around our region. Their mill and showroom is open weekdays and they pride themselves on being accommodating. If you cant find exactly what you’re looking for in stock, they’ll go out and find it — in the woods, a mushroom farm or an old barn – and mill it for you.
2290 NY-199, (845) 848-3040

3. Stissing House
In 1782, just after the end of the Revolution, Captain Cornelius Elmendorph founded a new settlement 15 miles from Washington’s camp as a connecting stop between Connecticut and the Hudson River. The Stissing House was the center of life in the new settlement, hosting gatherings of all kinds including many political meetings. Washington himself came through the notable Inn as did Roosevelt and the Marquis de Lafayette. Today, a beautiful restaurant helmed by husband and wife Patricia and Michel Jean calls the Stissing House home. Its traditional French-inspired dishes fit the historic destination with a peerless pastoral elegance. The amount of history and culinary talent that stews so effortlessly at Stissing House makes it not only the jewel of Pine Plains but one of the top places to visit in all the RI region.
7801 S. Main St., (518)-398-8800

4. Dutch’s Spirits at Harvest Homestead Farms
The fact that the Dutch’s Spirits distillery is located on top of a Prohibition-era bootlegging site is reason enough to head down the dirt road just outside of town to the secluded farm. The company’s namesake and spiritual patriarch, Dutch Schultz, made his stiff moonshine in a large underground concrete bunker. The new owners, which include one of Dutch’s descendants, have built a beautiful facility on top of that bunker to carry on the tradition in the light. The large modern barn is a farmstand and a tasting room, carrying the largest selection we’ve ever seen of New York-produced spirits in a single location. They also offer tours of the historic sites on the property and hold a number of events, especially this time of year. 
98 Ryan Rd., (518)-398-1022

5. Pine Plains Platter
The Platter is the best kind of small community café. They have the staples you expect but at a really high level. The menu is diverse and there are inventive specials that keep folks coming back. The café is owned by Irene and Jack Banning who also run the nearby Black Sheep Hill Farm. The couple hired Pine Plains native Amy Benack-Baden as manager and head chef, and she’s turned the quaint storefront into a delicious, family-friendly destination.
2987 Church St., (518) 398-0500

6. Chaseholm Farm
You may recognize the name Chaseholm from the farm list at the bottom of the menus at many of the best restaurants in the region. The dairy, cheeses and meats being produced by the farm’s grass-fed organic herd are all top quality and have become a staple in locally sourced dining. The multi-generational farm is now run by the brother and sister team of Rory and Sarah Chase. The siblings have kept the farm relevant by embracing modern holistic farming practices and by, above all else, working hard and making some really excellent stuff.
115 Chase Rd., (518) 339-2071

7. Lia’s Mountain View Restaurant
The Mirto family came to New York from Sicily in the ‘60s and, after moving upstate to Pine Plains, opened a classic Italian family restaurant with a menu as big as its breathtaking view of Stissing Mountain. It’s a true family affair as Lia, her siblings and their children all take part in running the restaurant. Brother Nick, sister Maria and Lia all have different duties in the kitchen. Along with the innumerable flavorful dishes the two sisters each make a cheesecake, so you can get a slice of each and let them know whose is better. In this healthy family competition, we win.
7685 NY-82, (518) 398-7311

8. Stissing Mountain
Pine Plains’ mountain isn’t just for admiring from afar. If you’re interested in a not-too-long yet intense hike there’s a great trail off Lake Road. The effort is well worth it, as the trail has a payoff in the form of a 90-foot firetower. Thirty feet taller than your average tower, it’s quite the ascent, especially if it’s swaying on a windy day. As you can imagine, there’s a spectacular 360-view from the top that goes on for miles. If you’ve got the gumption, climbing Stissing is worth the exertion.
Trail head located at 7 Lake Rd.

9. Pine Plains Memorial Hall
In many ways, this historic theater is the heart of Pine Plains. The Memorial Hall sits in the center of town, and for generations entertained its citizens, first with plays and later with films. Then for decades it sat dormant and crumbling. But it has now become a symbol of the town’s rebirth, and an energized grass roots effort to restore the facility is well underway. This summer they celebrated a huge fundraising milestone with a ground-breaking and community day that seemed to include every resident. There’s a lot of work to be done, but the energy behind the restoration of the Hall seems unstoppable.
2946 Church St., (518) 738-3409

10. The Inn at Pine Plains
With eight uniquely appointed rooms, the Inn at Pine Plains is the place to stay when exploring Dutchess County. Elegant, clean and accommodating, the Inn even has a signature breakfast sandwich as part of its locally sourced continental breakfast. The Inn is a continuation of Pine Plains’ history, a way-stop for travelers who soon find themselves entranced by the town.
3036 Church St., (518) 771-3117

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Posted by Jamie Larson on 09/25/17 at 08:10 AM • Permalink