Milwaukee

Think you know Milwaukee? You may be in for a surprise. The food scene has blossomed in recent years—from excellent fine dining to great grazing. And summer is the best time to visit: Bikers and joggers animate the lakefront paths, sailboats and kitesurfers glide across the horizon, and neighborhoods hum with life. Summerfest, the city’s gargantuan 11-day outdoor music festival, starts on June 27.

Madison

Exquisitely situated on an isthmus between two glittering lakes, Wisconsin’s capital is a haven for its outdoor-loving residents. The behemoth University of Wisconsin anchors the center of town, which may be why so much of the action clusters near the hilly campus and flows east toward Capitol Square. On Wednesdays in June and July, locals gather at the square for open-air concerts under the stars. On Saturdays, the Dane County Farmers’ Market—with its seemingly endless rows of vibrant produce and other locavore goodies—takes over. The market, perhaps the best in the country, is only one of many reasons to go.

Louisville

Long considered only a stopover on the way to Nashville, Louisville has exploded in the past few years—but still maintains its relaxed Southern vibe. New businesses pack East Market Street (see “Hot Hood,” below), bringing bona fide buzz to the downtown area, and neighborhoods are hopping with fun new destinations. The Kentucky Derby overruns the city in May, so do the smart thing and visit after the chaos subsides. You’ll find hotel rooms galore and the best seats at all the hot spots.