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.