Its setting may be rustic and its character may be historic, but the Berkshires village of Lenox — which recently marked its 250th anniversary — has plenty to offer refined and modern palates. Credit this to an arts scene that includes the world-famous Tanglewood and Shakespeare & Co.; haute house museums such as Ventfort Hall and Edith Wharton’s estate, the Mount; and a trove of grand hotels and resorts (Wheatleigh, Blantyre, Canyon Ranch, and Cranwell). Factor in Lenox’s inviting downtown and first-class nature escapes, such as Pleasant Valley Sanctuary, and it adds up to a lot of hungry visitors to feed. Luckily, the eateries here — fueled by farm-fresh Berkshires produce — rise to the challenge. So if you’re headed out that way, be sure to check out these top-notch Lenox, MA, restaurants.
Fine wine is the calling card of this sleek tapas bar, opened in 2012, which offers more than 100 vintages — more than three dozen by the glass. You’re sure to find the perfect pairing to go with whatever morsels you select from the lineup of Spanish and Italian small plates, salads, cheese and charcuterie plates, and handmade pizzas (our pick of the pies: caramelized onion, bacon, and crème fraiche). Named a 2015 Yankee Editors’ Pick for “Best Small Plates.”
The Instagram feed of this idiosyncratic little restaurant (28 seats) is downright addictive, since you can never guess what the creative mind of chef-owner Bjorn Somlo will come up with next. An elegant venison tartare. A simple tomato and citrus salad. Pork ribs with kale and pickled watermelon rind. There’s haute cuisine and comfort food, and somehow Somlo makes it all work together in a menu that changes nightly to make the most of what’s in season. Named a 2011 Yankee Editors’ Pick for “Best Seasonal Fare.”
One of the driving forces behind the recent rebirth of Great Barrington’s 20 Railroad Public House, Laura Shack, is the chef-owner of this longtime Lenox favorite. At both places she puts the focus on local, sustainable food, but never forgets that eating out should be fun, too. Couch-style seating, a long mahogany bar, and seasonal porch dining provide the relaxed backdrop for Shack’s sturdy (but never staid) gastropub fare: red wine–braised short ribs, grilled rainbow trout, roasted half-chicken. Named a 2013 Yankee Editors’ Pick for “Best Porch Dining.”
If you believe breakfast is the most important meal of the day, you’ll find no better place for it than this large and airy room perpetually filled with the buzz of happy diners. You can go elegant with a French-rolled omelet, sweet with croissant French toast, or hearty with an egg-and-cheese breakfast burrito. For late risers, Haven does a weekend brunch (featuring some tasty Benedict options, among other perks), as well as a weekday lunch service that brings out the sandwiches and salads, and burgers and burritos. Named a 2014 Yankee Editors’ Pick for “Best Berkshires Breakfast.”
As if we needed another reason to move to Lenox, in the off-season this classic Italian joint helps locals stay warm with specials such as $10 pasta nights and $25 three-course prix fixe dinners. But no matter what time of year it is, Frankie’s will make you feel at home with its hearty homemade pastas and other greatest hits of Italian-American cuisine: linguine with clams, spaghetti Bolognese, eggplant Parmigiana, lasagna, osso bucco, and much more. Dare you to try to save room for dessert.
Another one for vino lovers, Alta serves up simple, fresh Mediterranean-inspired entrées with smart wine pairing suggestions from its broad selection of vintages from around the world. (What goes with seared wild scallops or puttanesca bucatini — we’ll wonder no more.) No surprise, then, that Alta has also made a name for itself with an impeccable wine dinner series. It even does lunch with élan, grilling up paninis on Berkshire Mountain Bakery focaccia alongside salads, quesadillas, wraps, and more.
For comfort food at its most chic, head to this modern French bistro. You’ll forget all about meatloaf and mashed potatoes when you dig into the tender boeuf Bourguignon, savory coq au vin, or rich French onion soup — not to mention the stick-to-your-ribs steak frites. And crème brulée? Mais oui! All this, served up in a Church Street storefront that feels lifted from a corner of Paris, with its tiled floor, tin ceiling, mirrored walls, and red banquettes.
Before opening this shrine to all things chocolate in 2003, Joshua Needleman tempered his talents in France and later at New York’s La Maison du Chocolat (with stints at Canyon Ranch, Wheatleigh, and Cranwell thrown in for good measure). His accumulated expertise is reflected in the gorgeous bars, bonbons, cookies, cakes, and pastries showcased at this sit-and-stay-awhile café filled with casual wood chairs and sofas. Oh, and there’s ice cream and gelato, too — as well as sinful hot chocolates.
Did we miss any of your favorite Lenox, MA, restaurants? Let us know!
This post was first published in 2018 and has been updated.