Hillsdale, New York

From left: Hillsdale General Store and Village Scoop, jazz in the beer garden at Roe Jan Brewing Company.

through Hillsdale towards Great Barrington is a well-worn path for many visitors to the Berkshires. Nowadays, though, the traffic goes both ways, as Hillsdale has become a destination that Berkshire residents and visitors alike are drawn to. Indeed, the formerly sleepy farming town is now a second-home magnet with a vibrant artistic and commercial culture.

EAT/DRINK The Hillsdale House, right in the center of things, was revitalized after a makeover and is open for both takeout and indoor/outdoor dining. The historical restaurant, a piece of Columbia County since 1797, was first a stagecoach stop, post office, and a meeting place for revolutionary politicians. These days the tavern serves up a bevy of burgers, wood-fire pizza, and craft beers along with up-to-date small plates and vegan fare.

The Little Cat Lodge (formerly Swisse Hutte) is under new management and has a spiffy new look. Sip craft cocktails at the tavern or dine on alpine fare on the four-season terrace.

Satisfy your sweet tooth with The Village Scoop’s handcrafted ice cream; mocktails are also on tap at the “no-alcohol bar.” Or stock up on libations at Hillsdale Fine Wine & Spirits, tucked behind the local IGA.

Turn south on Route 22 and you’ll see O’s Hillsdale Country Diner on your left; the O is for Otto and the food falls in the “fine diner dining” category. A bit farther down the road, in a lovingly restored 1851 building, Roe Jan Brewing Company produces a rotating selection of beers that you can sample, purchase to go (in cans or growlers), or enjoy with elevated pub fare in the handsome eatery, and while listening to local talent at weekly concerts. Pups are welcome on the outdoor dining patio.

Traveling from the Taconic, you have your choice of two pit stops on Route 23 just east of Craryville: Random Harvest is a worker-owned neighborhood market, café, and community space that offers food and goods sourced directly from more than 70 local producers. In the former (and longtime favorite) Dutch Treat, Zinnia’s Diner has quickly become a destination spot for its inventive rendition of a “New England fish fry, Hudson Valley style,” as well as the location’s retro-meets-modern vibe and expansive yard with picnic tables for al fresco eating.

SHOP Interior designer Matthew White renovated an 1855 commercial building on the village square into what is now the Hillsdale General Store, with an emphasis on “old-style new” home goods and “useful and beautiful things for country life”— and a predilection for tureens and other vintage finds. White is largely credited with putting the historic hamlet on the map when he opened the shop back in 2011, garnering raves and earning himself a reputation as a certified style maven. He then expanded his empire with HGS Chef, which inhabits a can’t-miss pink house across Route 23 and offers cooking classes and an extensive cookbook selection, abundant cookware, and gadgets galore. Right next door, Tiny Hearts Farm, which organically farms 22 acres in Copake, sells its own cut flowers for pick-up or delivery in the area; better yet, sign up for its “flexible, free-choice” CSA membership, entitling you to free farmer-led tours and events along with flowers.

two amazing stores plus COOKING CLASSES COOKING CLASSES in Hillsdale NY!

Both open 10-5 Wednesday-Sunday

2635 Route 23, Hillsdale NY

GENERAL STORE 2642 Route 23, Hillsdale NY

In hindsight Passiflora was a veritable pioneer, hanging out a lonely shingle in 2009 and billing itself as “an eclectic mix of all things contemporary, quirky, and chic” (primarily housewares and personal care products, with an emphasis on local artisans); it’s still going strong.

And whatever your home needs may be, there’s a Herrington in Hillsdale who can help. For your construction and renovation supplies, visit Ed Herrington, Inc., just west of the intersection of Routes 7 and 23, and their Hillsdale Tile Design Center just east of it. Then, when construction is done, C. Herrington Home + Design, right at the intersection, with a beautiful retail shop and professional design services, can turn that house into the home of your dreams.

SEE Rodger’s Book Barn, off the beaten track but well worth the ramble, has over 20,000 “old and unusual” books on its well-organized shelves. East of town on Route 23, Berkshire Pottery has been crafting hand-made wares in a 19th century Dutch barn. Their pottery combines old-world craftsmanship with modern practicality.

The Workshop Experience is a series of hands-on classes on gardening, culinary arts, floristry, crafting, writing, and more by members of Hillsdale Workshop Alliance at various venues in Hillsdale (check the calendar for updates: theworkshopexperience.org).

STAY In addition to Little Cat Lodge, which has 14 rooms (including two suites), The Hillsdale House has three accommodations on the second floor. And though the pandemic forced the owners of landmarked The Washington House to cease operating the restaurant and tavern (after a 48-year-run), they have started offering five units via Airbnb for in-hamlet lodging.

For two takes on economy roadside motels, there’s the Holiday House Motel along Route 23, close to Catamount, or newly restored The Alander, in nearby Copake, for swankier sleeping arrangements.

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Farm-sourced eateries are just one of the (big) draws of this neighboring region in New York State. Also dotting the bucolic landscape are an impressive number of small-batch beer, wine, spirits, and cider purveyors—and navigating among them has just gotten a lot easier, thanks to the Scenic Sips Craft Beverage Tour. You have no fewer than five “circuits” to explore, each leading you down country roads with panoramic views and plentiful attractions (shopping, antiquing, hiking, you name it!) along the way. Whether you embark on just one route or the whole suite, delicious discoveries await. Visit columbiacountytourism.org for details and maps of the itineraries.