Cranwell Resort & Golf Course 55 Lee Rd., Lenox; 413/637-
1364, fax 413/637-0571; doubles from $89 in winter, $199 in summer. Pretend you're Gatsby at this old-style resort housed in 1890's buildings on 380 acres, with an 18-hole golf course, tennis courts, and a heated pool.
Apple Tree Inn & Restaurant 10 Richmond Mountain Rd., Lenox; 413/637-1477, fax 413/637-2528; doubles from $55 in winter, $155 in summer. Perched on a 22-acre hilltop estate across the road from Tanglewood, this 1885 house was Alice's Restaurant (made famous by Arlo Guthrie) until 1979. On the grounds are a pool, clay tennis courts, and a network of walking trails.
Blantyre 16 Blantyre Rd., Lenox; 413/637-3556, fax 413/637-4282; doubles from $295; open early May through early November. A 1902 Tudor mansion—the Berkshires' only Relais & Châteaux property—offering surprisingly friendly service and aristocratic style, with tennis, swimming, and croquet.
Red Lion Inn 30 Main St., Stockbridge; 413/298-5545, fax 413/298-5130; doubles from $100 in winter, $175 in summer. Rambling inn with a lovely veranda, a cozy lobby, and canopy or four-poster beds in most of the 110 rooms.
Williamsville Inn Rte. 41, West Stockbridge; 413/274-6118, fax 413/274-3539; doubles from $120 in winter, $140 in summer. A 1797 farmhouse converted to an inn in 1952. The secluded 10-acre property holds a beautiful sculpture garden (open in summer), pool, tree swing, and tennis courts. A favorite for weddings.
Canyon Ranch in the Berkshires 165 Kemble St., Lenox; 800/742-9000 or 413/637-4100, fax 413/637-0057; doubles from $1,204 per person for a three-night minimum stay. This outpost of Tucson's renowned health-and-fitness resort opened in 1989 and provides all the treatments and services you'd expect. At the heart of the 120-acre estate is Bellefontaine, a grand 1897 "cottage" modeled after Versailles's Petit Trianon.
Kripalu Center for Yoga & Health Route 183, Stockbridge; 800/967-3577 or 413/448-3400, fax 413/448-3384; dormitory beds from $77, private doubles from $118. The Retreat & Renewal package, included in all room rates, offers workshops in yoga, breathing, meditation, and DansKinetics. Set on a hill above the Stockbridge Bowl. Day passes available
Bistro Zinc 56 Church St.; 413/637-8800; dinner for two $70. Barely a year old, this stylish restaurant is straight out of SoHo, and draws an appropriately chic crowd with its gorgeous bar and excellent French bistro food.
Church Street Café 65 Church St.; 413/637-2745; dinner for two $60. A Lenox favorite, serving eclectic American food in several softly lit dining rooms and, in summer, on a shaded terrace. Unfortunately, the quality of the entrées has gone down a bit lately; make a meal of the excellent appetizers.
Spigalina 80 Main St.; 413/637-4455; dinner for two $60. Mediterranean cuisine served in a white clapboard house with a porch facing Main Street. Popular among Lenox's well-to-do for pre-Tanglewood dinners.
Baba Louie's Woodfired Pizza Restaurant 286 Main St.; 413/528-8100; dinner for two $25. Wood-fired pies with wholesome all-organic toppings. Virtuous as all get-out.
Bizen Japanese Restaurant & Sushi Bar 17 Railroad St.; 413/528-4343; dinner for two $75. Spectacular sushi and sashimi (the fresh fish is driven in daily from New York) served on chef Michael Marcus's own hand-crafted dinnerware. Prices are high but portions generous.
Union Bar & Grill 293 Main St.; 413/528-6228; dinner for two $50. Trendy hot spot with loft ceilings and sleek wood-and-aluminum interior, drawing an equal number of young hipsters and families (kids like the noise level). Very good New American food with French and Asian accents.
Lion's Den Main St.; 413/298-1654. Anglophiliac alert: The coziest pub in the county, in the cellar of the Red Lion Inn. Live music most nights—some of it intolerable, but hey, you can't win 'em all. Popular with tourists, always packed.
La Bruschetta Ristorante 1 Harris St.; 413/232-7141; dinner for two $60. Friendly and casual, with one of the longest wine lists in the Berkshires. Try the splendid bruschettas and risottos, and the osso buco.
Truc Orient Express 3 Harris St.; 413/232-4204; dinner for two $40. If you thought great Vietnamese food couldn't be found in a Berkshires hamlet, think again. This two-decade-old favorite, housed in a former warehouse, is still going strong.
Williamsville Inn Rte. 41; 413/274-6118; dinner for two $60. Elegant and eclectic New American and classic country dishes served in old-fashioned dining rooms.
Jack's Grill Main St.; 413/274-1000. A delightfully quirky place serving comfort food (pot roast, mac and cheese) in a former hardware shop outfitted with kitschy memorabilia and a model train. Great for kids, obviously.
Cactus Café 54 Main St.; 413/243-4300; dinner for two $50. The most authentic Mexican food around, which admittedly isn't saying much—but it really is excellent. The large tin-ceilinged dining room has a funky cantina theme.
Mezze 84 Water St.; 413/458-0123; dinner for two $60. The latest addition to Williamstown's refined dining scene, offering creative Mediterranean food. A post-show hangout for cast members from the Williamstown Theatre Festival.
Guido's Fresh Marketplace 1020 South St., Pittsfield, 413/442-9909; also at 760 S. Main St., Great Barrington, 413/528-9255. The Berkshires' finest grocery, with its own pasta shop, sushi bar, and bakery, plus a vast selection of meat and fish, from buffalo and venison to smoked trout.
Hilltop Orchards Canaan Rd., Richmond; 413/698-3301. Is there any greater joy than picking your own apples?Perhaps: the Vittori family also sells amazing cider and the tastiest pies north of Mississippi. Call ahead to order one. Or 15.
Daily Bread 31 Main St., Stockbridge; 413/298-0272. Unbeatable sourdough baguettes, pastries, and, occasionally, spinach-cheese calzones. Get there early.
Berkshire Ice Cream Scoop Shop 4 Albany Rd., West Stockbridge; 413/232-4111. Ben & Who?No, no, no—get local. It's amazing.
Nejaime's Stockbridge Wine Cellar Elm St., Stockbridge; 413/298-3454. Simply the broadest wine selection in the Berkshires, and great advice to boot. Two more locations in Lenox.
Mass MOCA (Massachusetts Museum of Contemporary Art) 87 Marshall St., North Adams; 413/664-4481. This huge 13-acre campus, created from a 27-building mill complex, opened last summer as a showcase for multidisciplinary works—which might never have existed without the "space, tools, and time for artists" that the institute provides. The emphasis is on large-scale sculpture and site-specific installations; artists on view include Dan Flavin and Robert Rauschenberg.
Chesterwood Off Rte. 183, Glendale; 413/298-3579. The country home of Daniel Chester French, best known for sculpting the Lincoln Memorial in D.C. The magnificent grounds are transformed into a sculpture garden from July to October.
The Mount 2 Plunkett St., Lenox; 413/637-1899. Edith Wharton's "first real home": a splendid 1902 mansion on 49 landscaped, lakeside acres. Tours available.
Arrowhead 780 Holmes Rd., Pittsfield; 413/442-1793. Herman Melville moved his family to this country estate to escape New York in 1850. He wrote Moby Dick here, in his study looking north to Mount Greylock—an undeniably leviathan view.
Clark Art Institute 225 South St., Williamstown; 413/458-2303. Housed in a perfect museum setting—with views of the Berkshire Hills to relax the eyes—the Clark's collection includes works by Renoir, Monet, Degas, Winslow Homer, John Singer Sargent, and Frederic Remington, among others.
Norman Rockwell Museum Rte. 183, Stockbridge; 413/298-4100. The world's largest collection of the underrated artist-illustrator's work, including every one of his Saturday Evening Post covers and a vast assortment of paintings and portraits. Seasonal exhibits profile other illustrators, and cartoonists.
Tanglewood Rte. 183, Lenox; 413/637-5165. Purportedly, one-fifth of America's professional symphony members have studied at Tanglewood. Critics may say its programming has become too indiscriminate, but this is still the quintessential American music festival, attracting virtuosi from Yo-Yo Ma to Itzhak Perlman and pop and jazz artists such as James Taylor, Cassandra Wilson, and Ray Charles.
Jacob's Pillow Rte. 20, Becket; 413/243-0745. The first, oldest, and possibly best summer dance festival in the country, held from June to August at a glorious hillside complex. The calendar reads like a directory of dance luminaries: last season brought Paul Taylor, Mark Morris, Trisha Brown, and others.
Shakespeare & Company at The Mount 2 Plunkett St., Lenox; 413/637-3353. Tina Packer's theater company is known for making Shakespeare accessible and reviving what Packer calls the Bard's "sheer joy and fun"; they also put on plays inspired by Wharton. Most productions are staged al fresco in the Mount's garden.
Williamstown Theatre Festival 1000 Main St., Williamstown; 413/597-3400. Eleven superlative productions in 11 weeks make this the nation's summer show-biz capital. Pretty Hollywood faces (last year, Gwyneth Paltrow and Ethan Hawke) attract audiences, and the staggering talents of Kate Burton, Karen Ziemba, Bebe Neuwirth, James Naughton, Blair Brown, and Harris Yulin keep them coming back.
Berkshire Theatre Festival East Main St., Stockbridge; 413/298-5576. Classics and premieres performed in a historic Stanford White-designed playhouse. Stephen Spinella appeared last year, and Eli Wallach crafted the title role in Visiting Mr. Green here before coasting into New York.