Where to Eat: The sleek Bentwood Tavern, at the Marina Grand Resort, is sceney on weekends, its bright dining room and outdoor terrace drawing yachters and young couples. Try the excellent tuna tartare with avocado, followed by a wood-fired pizza (600 W. Water St.; 269-469-1699; entrées, $8–$26). Brewsters Deli & Café is everyone's favorite local restaurant, with hearty Italian fare. Spring for the sampler appetizer plate, featuring mozzarella, prosciutto, and salami, followed by one of the creamy pastas: You've earned it (11 W. Merchant St.; 269-469-3005; entrées, $7–$15). The South Bend Chocolate Café, on New Buffalo's main drag, makes a mean hot chocolate and sells just about everything that can be coated in the stuff, including peanuts and strawberries (126 N. Whittaker St.; 269-586-2233). Soe, in Sawyer, is a good place to take a break from antiquing. A light and airy restaurant, it serves perfect macaroni and cheese and tasty burgers (12868 Red Arrow Hwy.; 269-426-4878; entrées, $8–$20). In Chicago, the unusual contemporary Italian-American fare at Aigre Doux—such as slow-cooked rabbit tagliatelle, lobster bucatini, and pan-seared black cod—has earned the restaurant rave reviews since it opened in 2006 (230 W. Kinzie St.; 312-329-9400; entrées, $12–$40). Or check out L2O, in Lincoln Park, a new seafood restaurant helmed by chef Laurent Gras (formerly of Fifth Floor in San Francisco). It serves such delights as Kampachi with kurobuta pork and sake (2300 N. Lincoln Park Ave.; 773-868-0002; four-course prix fixe, $110).

And Don't Miss: The Bill Lemmons Memorial Surfing Contest, the last Great Lakes shindig of the year, takes place on the first mid-October weekend with waves. It's held at Lakefront Park Beach, in Whiting, 19 miles south of Chicago (for details, go to thirdcoastsurfshop.com).
–Kate Maxwell