Once a run-down part of town, the East End of Portland, Maine, has recently found new life. Young artists, restaurateurs, and designers have taken over 19th-century cottages and Victorian "painted lady" houses. Here's where they spend their free time:

SHOPS Congress Street, formerly thrift-store row, is now lined with home-design stores. Angela Adams (273 Congress St.; 207/774-3523) is an Aladdin's cave of Op Art bags, mod stationery, and colorful handmade rugs beloved by Macy Gray. At the vest-pocket Ferdinand (243 Congress St.; 207/761-2151), artist Diane Toepfer carries sensuous papers, vintage table settings, and pillows by local artisans. The new kid on the block is 26-year-old Amelia Kutch and her Lost City Salvage (229 Congress St.; 207/828-0321), which sells $20 vintage alarm clocks and $2,000 stained-glass room dividers. Carlson & Turner Antiquarian Books (241 Congress St.; 207/773-4200) is packed with 70,000 secondhand books as well as Leonard Baskin prints; in the basement, owner Scott Wilson rattles out small print runs on an old-fashioned letterpress. A few blocks over, Botanico (83 India St.; 207/879-9006) is like a magical old conservatory—vintage pots and vases are filled with topiaries, sweet peas, and amaryllis.

CAFÉS Since caffeine seems to fuel the progress of the East End, the entire neighborhood converges on Coffee By Design (67 India St.; 207/879-2233) each morning. Their bicycles piled up outside, patrons huddle at tiny tables sipping rare Sulawesi Toraja and Jamaican Blue Voodoo. The Standard Baking Co. (75 Commercial St.; 207/773-2112) handcrafts breads and pastries—mouthwatering pear-frangipane tart, fig-anise loaf—in a World War II tank warehouse.

RESTAURANTS On Middle Street, Portland's restaurant row, chef Rob Evans (formerly of French Laundry and the Inn at Little Washington) has been luring Mainers from across the state to Hugo's (88 Middle St.; 207/774-8538; dinner for two $84). They come for his delicate combinations of organic local ingredients, such as saffron-infused, farina-encrusted Atlantic skate bouillabaisse. For no-fuss dining and unbelievable lobster stew, make a beeline for Norm's East End Grill (47 Middle St.; 207/253-1700; dinner for two $50).

INSIDER'S TIP For the best views in town, jog the Eastern Promenade, which overlooks the quirky 1807 wooden observatory atop Munjoy Hill.

Norm's East End Grill

Hugo's, Portland

Owner-chef (and James Beard Award–winner) Rob Evans may have trained himself to cook—but it’s not as if he just woke up one day and whipped up a batch of ocean-perfumed shrimp chips or salt-cured foie gras parfait. Rather, Evans worked his way from cruise-ship kitchens to Napa Valley’s French Laundry before taking over this longtime spot (keeping the original name, Hugo’s) in the center of Portland’s restaurant row. Now Evans’s wife, Nancy Pugh, expertly manages the comfy, if somewhat dated, black-and-maroon dining room, with a new bar menu and flat-screen TVs that telecast the ongoing action in the kitchen. But the real drama is on the plate. Evans is a master of creative cookery, blending seemingly unrelated flavors to tongue-tingling surprise, and seafood is his forte. Even a simple glass of rich, briny bouillon hides layer upon layer of flavor. And when Evans takes you down the gourmet rabbit hole with dishes like “ice wine vinegar snow cones” and “smoked milk chocolate mousse,” it’s best to go along for the ride. Any questions, just ask the ultrafriendly waitstaff, each of whom is fluent in Evans’s one-of-a-kind culinary language.