Taste & Tell

It’s me again—the new and somewhat opinionated local who unabashedly wrote about where I like to shop and eat in Lenox. (If you missed the article that appeared in the previous issue, you can read it online at berkshiremag.com.) I’m back again with restaurant recommendations scattered throughout the county map. 

This time, instead of hoarding all the suggestions myself, I tagged a crew of longtime locals and asked them one question: “Where are you going on repeat these days—for food, drink, or something sweet?” The answers did not disappoint.

To be fair, almost everyone protested that narrowing it down to one spot felt unjust, so if you know them and don’t see your favorite place mentioned, blame me, not them. Before we get into their picks—no surprise—I can’t resist slipping in my own current food crush.

You’ll find it by stepping into Widow Bingham’s Tavern at the Red Lion Inn in Stockbridge, which feels like walking into a time capsule—creaky wide plank floors, portraits that look like they start gossiping after dark, and history tucked into every corner. I’m there for all of it, paired with a smash burger that’s classically built, topped with the house Lion’s Sauce. It arrives perfectly blistered at the edges, cheese melted just right, and outrageously juicy in the middle. The deliciousness is vertically bookended by a potato bun that is buttered with beef fat, then toasted to a golden, crispy finish. It’s easily the best this side of anywhere. 

What follows are recommendations culled in no particular order. Here are the spots your friends and neighbors can’t get enough of. You can thank me by trying some of the tasty dishes and letting us know what you think, as well as sending us your own recommendations by emailing editorial@berkshiremag.com.

Berkshire Black Economic Council President and Executive Director A.J. Enchill and his team are on a steady loop of places that feel like local secrets. For a satisfying plate, they end up at BB’s Hot Spot at The Lantern in Pittsfield, loading up on jerk, ribs, and sides that feel like a full meal. For a midday pick-me-up, A.J. will duck into Dottie’s Coffee Lounge on Pittsfield’s North Street for a latte and a treat. Between meetings, lunch is usually whatever Just Kickin’ It Bar-B-Que in Dalton is pulling off the smoker. And on days when he needs a fresh pressed burst of energy, he’ll stop at We Got The Juice in Adams for something cold, bright, and green.

MASS MoCA Executive Director Kristy Edmunds is, by her own admission, devoted to restaurants in North Adams. She’s reluctant to play favorites, but if you’re looking for her these days, start at Casita on the museum campus or The Airport Rooms at TOURISTS, where the new chef, Ety Mundeke-Atwood, is, Edmunds insists, “fabulous.” And on Tuesdays, it’s basically a standing date with STATE Food + Drink at Greylock WORKS, where Tu Le’s Vietnamese menu—“truly glorious,” in her words—has become a non-negotiable ritual.

18 Degrees Executive Director Stephanie Steed keeps The Roasted Garlic in Pittsfield in business at lunchtime. The room is casual and reliably buzzy—the sort of place where you can debrief a meeting over a basket of fries and not feel rushed. Her default is the veggie burger with sweet potato fries, but on days when she’s feeling “a little extra” (and really hungry), she graduates to the verdure pizza (vegetable pizza). “Yum!” she says, half endorsement, half confession.​

Berkshires innkeeper Claire Collery, owner of the newly renamed Avaloch Inn (previously the Apple Tree Inn), has a standing date with the farfalle alla contadina at Acqua al 2 in West Stockbridge—the one pasta that made her eat her words about hating bowties. Co-owner Valentino Pagliari makes sure the noodles are boiled in aggressively salty water, so they arrive properly al dente, then swaddles them in a silky, deeply savory mix of roasted vegetables and winter herbs that gives vegetarians the kind of umami hit they’re usually denied. “It’s become my ultimate comfort pasta,” Collery tells me, confessing that she even breaks tradition (and, allegedly, Valentino’s heart) by ordering a ball of burrata on the side and dotting it over the top. 

Ever had a filet with blueberry sauce? Worth it for the plot twist alone, if I say so myself. But the real non-negotiable is dessert—it’s an Italian restaurant, after all. 

Berkshire-born Jim Hatch is a descendant of the Phelps Stokes family of Shadow Brook, now Kripalu. His go-to indulgence? Hands down, it’s takeout from Chef Aura Whitman at Berkshire Mountain Bakery in Pittsfield. His order is almost always the quiche of the day—think wildly creative, never-the-same-twice combinations—and let’s just say more than one usually ends up in his fridge for later.

Jacob’s Pillow Chair Mark Sena considers Prairie Whale in Great Barrington the restaurant that best encapsulates the region’s food culture. Plus, the space feels as warm and unpretentious as it is stylish. He goes for the true farm-to-table experience: a changing menu built on locally sourced ingredients and unfussy, deeply creative cooking from Mark Firth, whom he describes as a “legendary restaurateur,” and his team. Sena also will happily detour to Gedney Farm in New Marlborough for its swoony setting, inventive menu, and genuinely interesting wine list. Closer to his home in Monterey, he is fiercely proud of—and devoted to—the Roadside Café, part of the 103-year-old Gould Farm therapeutic work program.

Former Massachusetts Governor Deval Patrick is a breakfast regular at Otto’s Kitchen and Comfort on Court Square in Pittsfield. The room has that lived-in, downtown diner energy—coffee cups always in motion, a little clatter, everyone half-known to one another—and a team he describes as unflappable with unfailingly great attitudes. His grandson is loyal to the corned beef hash with a runny egg on top, the kind of classic that feels like it’s been on the menu as long as Court Square itself. 

South Egremont Spirit Shoppe co-owner Dan Thomas keeps it comfort-and-Great Barrington-centric. For an easy, low-key night out, he heads to the bar at Number Ten for a Caesar salad and a burger or fried chicken—with great fries and a “killer” Manhattan in the mix. For takeout, he swears by the authentic Southeast Asian fare at STEAM Noodle Cafe, which he reminds us is cheaper than a flight to Thailand: gyoza pie to start, then either khao soi or the noodle chicken salad, always with extra chili oil. For something sweet, it’s Pixie Boulangerie “always” for Basque cheesecake, and Odd Bird Farm Bakery for treats, especially an oatmeal cookie with apricots and jam that he describes as “dangerously good.”

Music Inn founder David Rothstein has loved The Old Mill (now called The Mill and touted as an oyster bar and lounge) in South Egremont for half a century, thanks in no small part to his long friendship with chef-owner Terry Moore. For Rothstein, it’s all about the bar. “You’re literally drinking beneath massive old beams in an authentic mill-barn space,” he says. The fireplace was a blacksmith’s forge in 1797—the dining room is where they’d shoe oxen. And then there’s the clincher: the chicken liver pâté that’s still proudly on the menu after all these years.

Clean-beauty OG and namesake founder Jane Iredale has a standing crush on Pleasant and Main in Housatonic. She says, “If you want a paper-thin crêpe and the thrill of spotting the perfect antique teacup or glass while you wait, this is your place.” Owner Craig Bero is a devoted forager—on lucky days, he’s serving trout from an undisclosed, pristine river with wild watercress, plus wild mushroom volauvents that Iredale swears are the best, all told alongside a stream of stories that last as long as the time you have to linger. 

Folk legend Arlo Guthrie doesn’t get out much these days, but when he does, he’s not chasing tasting menus. There are a few South County spots he’ll hit on occasion, yet more often than not he just heads down the road to the Route 8 Pub in Becket—a low-key room of regulars, neon beer signs, and no pretense whatsoever. It’s friendly, firmly local, and proudly un-gourmet: nothing fancy, just solid burgers, cold beer, and “very decent” food, which is exactly the point.

Farnsworth Fine Cannabis Company founder and CEO Alexander Farnsworth recently converted to the sweeter side of things thanks to his brother, who showed up with a maple walnut pie from Pastries by Hanna for his birthday. (Find out more about the one-woman wholesale bakery out of Canaan, Connecticut, at pastriesbyhanna.com.) “I was a lifelong pecan pie loyalist until that first slice, and now I’m fully converted,” says Farnsworth. Right now, he can also be spotted at the newly open ilse coffee on Railroad Street chatting up co-owners Lucas Smith and Rebecca Grossman, They take their coffee seriously, and so does he (at least some of the time, he quips). Closer to home, he probably logs the most dinners at Cafe Adam with his partner, Adam Lippes, where they keep going back for the Korean BBQ ribs.

The Mount Executive Director Susan Wissler is often spotted on Main Street in Lee at lunchtime. Her regular spot is Starving Artist Creperie & Cafe, where the relaxed atmosphere, friendly service, and range of organic, vegan, and vegetarian options make it an easy habit. Her current obsession is the spicy turkey Reuben crêpe, made singular by Hosta Hill’s curried sauerkraut, which layers Indian and Korean flavors onto an otherwise all-American standard.

Multicultural BRIDGE CEO and Founding Director Gwendolyn VanSant measures out her calendar in meals from North to South County with family, colleagues, and friends. Mezze Bistro + Bar in Williamstown is her pick for milestone celebrations, and Heirloom Lodge in West Stockbridge when she wants a wine-forward dinner.

something quieter, it’s Once Upon a Table in Stockbridge; Koi in Great Barrington for a lychee martini; Xicohténcatl Mexican restaurant in Great Barrington for a margarita and camarones machos; and Brava in Lenox for cocktails and small plates. On workdays, she’ll swing by Guido’s Café Rena in Great Barrington for a ginger-lemon shot and seasonal matcha or smoothie. Her true favorite, though, is her own Solidarity Kitchen at BRIDGE in Great Barrington, where she’s hosting or gathering around food nearly every week—because, for her, “food is where culture, care, belonging, and joy meet.”