Hillsdale, New York

From left: Passiflora and The Hillsdale House.

from the Taconic 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 secondhome 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.

A stone’s throw away, 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. Beloved O’s Hillsdale Diner has changed hands and is now Sweet Peas Country Diner. And comfort-food shop Cook & Larder has opened in the former Crossroads location for sweet and savory prepared foods and grab-and-go items.

The Little Cat Lodge (formerly Swisse Hutte) is under new ownership and has a spiffy new look. Sip craft cocktails at the tavern or dine on alpine fare on the fourseason terrace. Or stock up on libations at Hillsdale Fine Wine & Spirits, tucked behind the local IGA.

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.

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.

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 wellorganized shelves. East of town on Route 23, Berkshire Pottery has been crafting handmade wares in a 19th century Dutch barn. Their pottery combines old-world craftsmanship with modern practicality. Roeliff Jansen Park, located one-half mile south of the town center on Route 22, offers multiple (gentle) walking trails on a 300-acre farm with four-season views; it’s a favorite among dog walkers.

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-yearrun), 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.

Located on Main Street in Chatham, N.Y., the single-screen Crandell Theatre lives up to its motto: Small Town. Big Movies. It has also managed to preserve its historic charm— as the oldest of its kind in Columbia County—while becoming a progressive center for mainstream and indie screenings, including as host of the nationally renowned FilmColumbia festival. Like many small-town venues, the Crandell has not returned to its pre-pandemic 365-day showings, but there’s plenty to keep you coming back to this palatial spot—and picturesque village. Check crandelltheatre.com for film times.

Hillsdale, NY: 518.325.3131· Marble & Tile Design Center: 518.325.5836 Lakeville, CT: 860.435.2561· Hudson, NY: 518.828.9431