Heading east on Route 23 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, or stops before it gets there, as Hillsdale has become a destination that Berkshire residents and urban visitors alike are increasingly drawn to.
The formerly sleepy farming town is now a second-home magnet with a vibrant artistic and commercial culture in which part-timers are as invested as year-rounders. At this writing, in early August, most Hillsdale restaurants and stores are open but with limited hours and COVID restrictions. Passiflora is open Wednesday through Sunday, 11:00 am to 5:00 pm, and offers curbside service for items ordered by phone or online. It hung out a lonely shingle in 2009, 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); 11 years later it’s still going strong. 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 stylish, functional housewares. Currently, it is open Wednesday through Sunday, 10 a.m. to 5 p.m. The same building is also home to Cross Roads Food Shop, a farm-to-table restaurant that serves a great breakfast. Crossroads is now open Thursday through Sunday, 8:30 a.m. to 2:30 p.m. They’re serving breakfast all day, and lunch beginning at 11:30. Following New York State COVID rules, their inside tables are at half capacity; take-out customers are welcome to eat at their charming outdoor tables. At this moment, they are not taking reservations.
White then went a step further, starting up HGS Chef, which sells cookware and offers on-site cooking classes with top chefs, in another made-over building across the street. HGS Chef is currently open Wednesday, Thursday and Friday 11 a.m. to 3 p.m., and Saturday and Sunday 10 a.m. to 5 p.m. No in-store classes right now, but HGS Chef has successfully experimented with Zoom classes and is likely to continue that. Right next door, Tiny Hearts Farm, which organically farms 15 acres in Copake, is selling vegetables and flowers, primarily to their CSA subscribers.
The latest arrival on the scene is the Roe Jan Brewing Company on Anthony Street not far from the town center: fresh beers and a menu with steaks from a wood-fired grill and tasty salads, along with wines and cocktails. Roe Jan is open (and lively) Monday, Thursday and Friday 5 to 9 p.m., and Saturday and Sunday noon to 9 p.m. They’re serving indoors and out, all at respectable distances. Reservations for outdoor tables are only accepted the day of. And you can still sit at the bar, despite the acrylic shield that protects you.
The Hillsdale House, right in the center of things, came alive last year after a makeover. After their recent COVID closing, they are offering both indoor and outdoor seating, as well as takeout Monday, Thursday and Friday 4 p.m. to 9 p.m. and Saturday and Sunday noon to 9:00 pm. Same day reservations are accepted. Unfortunately, the Village Scoop, which the owners of Passiflora created in the space formerly occupied by a tattoo parlor to serve non-alcoholic cocktails as well as exceptional artisanal ice cream, is temporarily closed. But, if your hair has gone to hell during the pandemic, you can still get a haircut in Hillsdale, too, at least if the pole outside Trudy’s Beauty Shop is spinning; men’s haircuts $18, beards extra, basic women’s trim, $19.
Not all the action is in the village. Rodger’s Book Barn, off the beaten track but well worth the ramble, has 50,000 “old and unusual” books on its well-organized shelves. It’s open Friday, Saturday, and Sunday, 11:00 am to 4 p.m., with masks and social distancing required, and Monday and Thursday mornings by appointment. Mirror Mirror, located on Route 23 between the Route 22 junction and the town center, offers both vintage clothing and housewares and is open Thursday through Saturday 8:00 am to 4:00 pm, and Sunday 10 a.m. to 3 p.m. And Sideshow Clothing Company has moved from Hudson, N.Y., to the space right next to Mirror Mirror, buying and selling vintage clothing both in the shop and online.
The Swiss Hutte Inn & Restaurant, on Route 23 near the Massachusetts line, is a popular spot for lunch and dinner; Zurich native chef Gert Alper presides over a marriage of European cuisine with locally sourced ingredients. They’re open Wednesday through Saturday 5:00 to 8:30 p.m., and Sundays 1 to 7 p.m., with tables both inside and out (reservations highly recommended) and also take-out. The charming inn, by the way, is also open.
Turn south on Route 22 and you’ll see O’s Hillsdale Country Diner on your left, open daily 7:00 a.m. to 9:00 p.m.; the O is for Otto and the food falls in the “fine diner dining” category. The local Stewart’s is there too, open as usual seven days a week 5 a.m. to 11 p.m., if you need to refuel your car or yourself.
And 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. Open 10 a.m. to 4 p.m. Monday through Saturday.
For D.I.Y. food, try the Hillsdale Supermarket (“home of the one-dollar sale”), a classic full-service IGA right near the village square. It’s locally owned and has an excellent meat department; stock up your larder for less. Spend your savings at Hillsdale Fine Wine & Spirits, right behind the IGA. Random Harvest, open Thursday through Sunday 11:00 a.m. to 6:00 p.m. and online, is a worker-owned neighborhood market, café and community space that offers food and goods sourced directly from more than seventy local producers; if you’re coming in from the Taconic, it’s a convenient stop just east of Craryville on Route 23.