The Towns of the Berkshires

The grand estates and hotels of the Berkshires might be hushed, but the towns in which they sit — Lenox and Great Barrington — are vibrant, quirky and hip. Lenox, which is home to Wheatleigh, Blantyre and also Tanglewood and Shakespeare & Company, is a charming New England village with plenty of cute cafés, excellent restaurants and lovely shops. The larger town of Great Barrington, about a 15-minute drive south of Lenox, is home to some fabulous antiques stores as well as more great eateries, both casual and refined.

Where to Stay

Wheatleigh

is an exquisite Italian palazzo–style stately home turned hotel that offers a secluded, intimate stay with an emphasis on haute dining and quiet. A 5-minute drive away, Blantyre is a stately Scottish-style manor house that transports guests back to the early 20th century, when days were filled with croquet and lawn tennis and evenings were black-tie affairs complete with multi-course dinners and piano music by candlelight.  The Berkshires outpost of Canyon Ranch is also located in Lenox, but guests tend to stay on property and focus on the Ranch's offerings of activities, classes and lectures.

Where to Eat

In Lenox, Nudel (37 Church St.; 413-551-7183) is the foodie favorite for dinner, serving seasonal cuisine in innovative ways. Alta (34 Church St.; 413-637-0003), across the street, is a little less refined but also delicious, offering excellent small plates as well as a full menu that pairs nicely with the impressive wine list. For lunch, Church Street Café (65 Church St.; 413-637-2745) has delicious soups, salads and sandwiches and a sun-filled dining room. The hot spot in town for breakfast, brunch and coffee and treats throughout the day is undoubtedly Haven Café and Bakery (8 Franklin St.; 413-637-8948), a seriously cheerful spot offering coffee, pastries and homemade granola.

There are more choices down the road in Great Barrington, including Café Adam (420 Stockbridge Rd.; 413-528-7786) set in a casual, barn-like space but serving refined dishes like sirloin with caramelized shallots and black lentil jus and grilled Canadian wild boar loin with bourbon-soaked cherries and apples and crispy sage steel-cut oatmeal. The Prairie Whale (178 Main St.; 413-528-5050) comes from former Brooklynite Mark Firth, who was the force behind the borough's famed Marlow & Sons and Diner. The refined cuisine in the cozy restaurant includes local produce and offerings like deviled eggs with dill, herb mayo and trout roe and chicken liver pâté with cornichons and country bread. Rubi's Coffee & Sandwiches (264 Main St.) specializes in grilled cheese sandwiches and has a menu of just these family favorites, including highlights like the French onion "soup" sandwich, which includes stewed onions in beef broth on Pullman bread. Meat Market (389 Stockbridge Rd.; 413-528-2022) serves lunch and hosts occasional dinner events featuring, you guessed it, meat. Specialties include burgers, sandwiches and paté.

What to Do

There is a lot to do in the way of outdoor and cultural pursuits in and around Lenox. In the summer, Tanglewood Music Center (301 Massachusetts Ave.; 617-638-9230) is the home to the Boston Symphony Orchestra and features al fresco performances throughout the season. Edith Wharton's former home, The Mount (2 Punkett St.; 413-551-5111), where she often entertained her friend Henry James is open to the public and hosts events. Another wonderful Gilded Age home worthy of a visit is Naumkeag (5 Prospect Hill Rd; 413-298-8138), a gracious, shingle-style manor home of the Choate family with beautiful gardens, including a Chinese garden, rose garden and linden alleé. Shakespeare & Company (70 Kemble St.; 413-637-1199) a theater organization, puts on plays by the Bard as well as more contemporary playwrights. The Jacob's Pillow Dance Festival has occurred each summer since the 1930s, when it was founded by Ted Shawn, an early pioneer of modern dance. It hosts an impressive line-up of myriad styles and companies, from two-person experimental dance to such established companies as Mark Morris Dance Group. (358 George Carter Rd., Becket; 413-243-0745).

Before or after a visit to Jacob's Pillow, many stop in to Dream Away Lodge (1342 County Rd., Becket; 413-623-8725) for a meal. The historic spot—which boasts a restaurant, bar, lounge and casual theater-type space—has been a hot spot for musicians since the 1970s when Bob Dylan was a regular.

To the north of Lenox, Clark Art Institute (225 South St., Williamstown; 413-458-2303) and Mass MOCA (87 Marshall St., North Adams; 413-662-2111) are two of New England's preeminent art museums.

Where to Shop

In Great Barrington, Rubiner's Cheesemongers & Grocers (264 Main St.; 413-528-0488) sells artisanal cheeses and accompanying preserves, crackers and various gourmet sundries. Chelsea + Co. (434 Stockbridge Rd.; 413-528-1888) is a rabbit warren–like barn of vintage furniture and clothing, while Berkshire Home & Antiques (107 Stockbridge Rd.; 413-429-6317) offers more high-end antiques. Dabney McAvoy (635 Main St.; 413-528-3600) sells more contemporary decorative accents, textiles and ceramics and One Mercantile (8 Castle St.; 413-528-1718) specializes in kitchenware and stationary and has a lovely assortment of gifts like colorful mason jar glasses and squirrel-printed baby onesies. In Lenox, there are a handful of lovely boutiques, especially the sophisticated Design Menagerie (26 Housatonic St; 413-551-7528) which stocks a well-curated mix of minimalist furniture, coffee table books, jewelry and gorgeous leather accessories. For beautiful blankets, ranging from Italian cashmere to Irish tweed, and lovely pillows and knits, visit MacKimmie (67 Church St, 413-637-9060), and don't miss nearby Willowbrook Home (69 Church St #1; 413-637-0340), which carries lovely glassware, soaps, candles and other elegant gifts.