Hidden and Not So Hidden in Hillsdale, NY

  |  November 2, 2015

We are traveling south on Rt 22 NY at 6:04 am on a fall weekday morning in Central Columbia County NY. Earlier in the summer at this hour on this route one can see the stunning hills and rolling meadows that grace each side of the road, but today it’s pitch black. At the intersection of Rt 22 NY and Rt 23 NY, there is the only traffic light for miles, and a sign that says Hudson 23 miles west, Millerton 19 miles south, and Great Barrington, MA 12 miles east. This is known as the “crossroads” in Hillsdale, NY – a special town in “CoCo.”

It’s not Hudson and it doesn’t have a “Little Apple” scene going on. It’s not as cool as or chic as Great Barrington and it doesn’t need to be. It has more in common with Millerton, but doesn’t seem to be trying quite as hard to be hip. It’s Hillsdale… and it has its very own magical vibe set against a truly stunning backdrop, standout gorgeous even in a region known for natural beauty.

c herrington

C. Herrington Home and Design

There’s a lot going on in this rural town of about 2,000 residents in the daytime. Working farms abound, as do tradesmen supporting the weekend homeowners from downstate (NYC is 2-1/2 hours away). However in the dark at 6:04 am, the main action is at Stewarts’, the only place in town that’s open. Serving coffee and baked goods (like their famously addictive glazed lemon donuts), it differs from other roadside convenience stores because it’s part of a regional chain famous for its old-fashioned soda pop and hand-packed ice cream, and also because it has a small seating area, where you will usually find more regulars than tourists – the mix of characters unique to Hillsdale. On this Tuesday, David Wurth, Chef/owner of CrossRoads Food Shop, is sitting in a bright orange booth with a large Stewarts’ coffee, reading a newspaper with great concentration. He opens his restaurant around the corner at 8:30 am. But he enjoys his coffee amongst the parade of local early risers here; his morning ritual before he heads off to prepare his infamous breakfast sandwich (two eggs, cheese with onion and tomato relish on hearty 7 grain bread) for his own regulars at his noted farm-to table spot that also has killer coffee.

Kelly, the trusty early morning shift manager at Stewarts’ happily greets all that enter including the local water pump engineer, the house-renovating-lesbian couple on their way back to the city after a long weekend, the local landscape contractor stocking up on ethanol-free gas for his equipment. The day is just beginning in history- steeped Hillsdale with its amazing character… and characters. The town historian, Peter Cipkowski, can tell you all about Edna St. Vincent Millay’s visits to Hillsdale, her poet friends and the buildings and industry that are/were in the area.

Known to some as the gateway to the Berkshires and what some repeatedly refer to as God’s Country, it has views of the Catskills to the west and the Taconic range to the east. It’s main street is Rt 23 NY and at first glimpse looks like a set for an 1800’s period film starring Renee Zwellweger and a mountain or two. Blink and you will miss the war memorial, followed by The Mount Washington Hotel and Town Hall. But get out of your car and discover some very interesting things on the towns corners and curves.

Home Chef

The newly opened HGS Home Chef across the street from the Hillsdale General Store.

Below are the reasons why so many adventurous types that drive through Hillsdale stop and take it all in (and then look for a real estate agent).
In the Hamlet of Hillsdale all of the places below are within walking distance of each other:
• Eat breakfast or lunch at: CrossRoads Food Shop then have dinner at The Greens at nearby Copake Lake.
• Take a cooking class on the art of Dumplings From Around the World at the brand new HGS Home Chef directly across the street from The Hillsdale General Store, where one can stock up on everything from martini shakers to squirrel nuts to gardening gloves. Upstairs there are world-class antiques sourced by the owner of the HGS, who happens to be a well-known NYC based interior designer.
• Score a framed photo of a vintage Farmall Tractor by Lawrence Kalfus or some printed farm animal throw pillows at the interior furnishings mecca of C. Herrington Home + Design
• Hang out at: Brown & Jackson Space. A Hillsdale/Brooklyn based design consultancy specializing in interiors, environments and events for both client and self-initiated projects.
• Check out the current art offerings at LABspace and Neumann Fine Art
• Hike at Roeliff Jansen Park‘s meadow and sample (very) local food at the Saturday Farmer’s Market.
• Stay with Doug and his miniature pinscher Dean in a Classic Victorian Farmhouse on Coldwater St. with designer chickens across the street.
• Get a Root Beer Float at The Village Scoop, before you snag a Blue Crackle Glass Lamp at Passiflora for your home or a friend.
In and around the bucolic town of Hillsdale: visit the Hawthorne Valley Farm, the renowned Rodger’s Book Barn, enjoy downhill skiing and snowboarding at Catamount. Hike to Sunset Rock and play the “name the Catskills’ peak game. Then get some wienerschnitzel at Swiss Hutte.

And additionally there are these HDale places and things:

Northeast Farm access and their groundbreaking organic farms in Copake (that’s a story unto itself)
• The incredible Camphill Village in Copake (biodynamic farm, workshops, bakery etc)
• Taconic State Park which has Bash Bish Falls and the Historic Ironworks –
Inn at Green River – great quality inn in Hillsdale
Silvanus Lodge, fun and affordable
Harlem Valley Rail Trail, great in any season for biking, walking or cross country skiing or snow-shoeing
Copake Auction House
• Margaret Roach’s fabulous (and much followed) garden advice blog
Hillsdale Fine Wine and Spirits is a brand new addition to town and it’s located behind the IGA supermarket in the heart of Hillsdale. Please stop in and see Meghan McCann the resident expert who will advise you on their well-curated selection.

Hillsdale Wine store

About Joanna Virello

Joanna Virello lives in Hillsdale, NY and Fort Greene in Brooklyn. She graduated from NYC's School of Visual Arts and works as a PR and marketing executive with over 15 years of experience. She specializes in creating campaigns for travel, design, food & beverage and technology. She also worked in publishing where she created and branded large and well-attended food and cultural events in New York. Currently she is busy restoring a 1987 27 ft. Airstream Sovereign on 5 acres of the 1961 custom ranch that her better half is renovating in Hillsdale.

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