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Roads Less Traveled: Out of the Way Places We Love, Part 2

By Jamie Larson

Last week we explored some of our favorite out-of-the-way main streets on the New England side of the RI region. This week we’re over in New York, giving due credit to some less-talked-about town centers in Columbia and Dutchess counties. One of the things we love most about the area is how agrarian heritage and a growing metropolitan cultural influence have blended (even if not always easily) to build communities that support all types of enterprises, from farms to art galleries. The binding thread seems to be a passion for quality.

Columbia County

Philmont

Philmont is the little village that could. Climbing along the sides of Philmont’s steep Main Street are businesses supported by a community that has been keeping the town chugging along with an admirable amount of civic tenacity. Philmont Beautification is a grass roots organization that has been working hard on major revitalization plans, hosting events, cleaning up the town and promoting business growth. They host the Farmers Market, one of the best around, and the Philmont Market Co-op and Cafe is coming soon. Though the store isn’t open yet, its mobile, bright green Curbside Café offers some simple, delicious food that reflects the local farm fresh values of the future Co-Op.

Philmont is also home to the highly praised Local 111 restaurant, helmed by Josephine Proul. Her kitchen manages to create a heightened dining experience while letting the quality of local produce and meat shine through. Just down the hill is The Main Street Pub, run by Proul’s mother, Elizabeth Angello. The pub has been around for generations and is in many ways the social hub of the village. You can also grab a slice at Gabriel’s or eat and get a room at the beautifully restored Vanderbilt House, which is now back in the hands of the ancestors of the family that originally ran it.

Old Chatham

The center of Old Chatham is less of a main street and more of a crossroads where Albany Turnpike and Route 13 meet. Jackson’s and The Old Chatham Country Store and Café sit cattycorner from one another. Jackson’s is a county institution, old and cavernous with an ambience that somehow encapsulates vintage Columbia County. It has a great old bar and a dining room offering road house classics done right. The Country Store is as much a historic landmark but has undergone a bit more modernization. Its farm-to-table menu is as fresh and beautiful as the light that pours in from the big old windows. Make it a breakfast and lunch destination, and keep in mind that they offer a Sunday dinner-to-go (you need to order it by Wednesday night).

The name Old Chatham may be known to you because of the much-loved and widely distributed sheep cheese and yogurt produced at the Old Chatham Sheepherding Creamery just outside of town. If you’re in the mood to pick some up after lunch, they have a self-serve, honor-system shop at the farm. You can also go shopping for all your alpaca wool needs at Spruce Ridge Farm. The happy alpacas themselves surround the barn and shop, and make for a really cute place to visit (kids love it). And finally, if you need to work up an appetite or are just looking for some native birds to peep, the Wilson M. Powell Wildlife Sanctuary has a really enjoyable trail. It’s just long enough to make you feel like you’ve done something productive without knocking you out and the trail peaks at a splendid overlook. Afterwards you’ll have earned your lunch and/or cocktail back at the crossroads.

Dutchess County

Amenia

Amenia feels like a distant border town where the edge of two kingdoms meet. It sits in the beautiful southern foothills of the Berkshires, yet is also home to the last train stop on the Metro North Harlem line from New York City. The tracks literally end a few yards north of the station. This convergence of cultures and socioeconomic classes has caused some chafing over the years (as evidenced by the fight over the creation of a massive gated resort community for the super rich). But Amenia is also home to some fabulous restaurants and attractions that appeal to both locals and train commuters alike.

One successful new addition is the Four Brothers Drive-In Theater next to the regional institution Greek restaurant and pizzeria of the same name. The family-run drive-in has been drawing in the crowds with blockbusters, classic movies, daytime events and a modern concession stand. And you can get anything from the restaurant next door brought to your car, which is so cool it feels like you’re doing something against the rules.

Amenia has a number of top-notch restaurant options as well. Serevan, in a historic farmhouse, uses local ingredients to craft dishes as delicious as they are beautiful. Monte’s Kitchen and Tap Room is a transplant from Brooklyn, run by the family that brought you Monte’s there, but offering a menu that’s more “Hudson valley farm to table” than red sauce over spaghetti. They also run the health food and specialty store, Monte’s Heath Nut Hut. Amenia may look sleepy, but there’s a lively current running through town that’s fun to ride.

Pine Plains

We spend a lot of time shopping and partying with the great folks at the Hammertown Barn, just a little down the road from Pine Plains’ Main Street. More than just a furniture and lifestyle store, Hammertown and its founder Joan Osofsky have been great champions of local businesses, farms and charities for nearly three decades. 

Another town institution you may already know is the Stissing House. Built in the 1700s and a way station for the likes of Presidents Washington and Roosevelt, the Inn is the historic heart of Pine Plains. The restaurant is perhaps the best French restaurant north of Yankee Stadium, thanks to Chef Michel Jean.

Church Street is where the action is. Along with the Stissing House there’s also the seriously good Schapira Coffee and Tea Co., Johanna’s Raw Foods and The Pine Plains Platter. One of the most interesting goings on other than food is the restoration of the historic Pine Plains Memorial Hall. Aiming to spur community development through arts and other civic programing, boosters of the project are extremely active. The hall, they say, will be a centerpiece that will draw even more attention to the town. They’re holding a benefit concert upstairs at the Stissing House featuring the Jacques Thibaud Trio and flutist Eugenia Zukerman on July 3 — yet another reason to pile into the car for a good old-fashioned day trip.

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Posted by Jamie Larson on 06/20/16 at 08:35 AM • Permalink