Why it's so great: This town of about 1,600 people is home to two of the biggest tourist attractions in Wisconsin: Taliesin and The House on the Rock. Taliesin was built by famed architect Frank Lloyd Wright in 1911, though it was rebuilt a number of times due to fires, and he used it as his peaceful summer home and studio for most of his life. The House on the Rock, on the other hand, is a kind of frenetic museum of insane collections. If the self-playing orchestra doesn't creep you out, then the room of antique dolls certainly will. The glass "infinity room" that juts out over a ravine for a panoramic view is also scary, but in a less nightmare-inducing way.
Must-eat foods: Smoked trout dip at Freddy Valentine's; trout dinner, available some Fridays, or any deli sandwich at Driftless Depot.