Why it's so great: The town of Bayfield on the shore of Lake Superior is the jumping off point for the Apostle Islands National Lakeshore, which has some of the best kayaking in the world. There are sea caves -- that turn into ice caves if the weather cooperates in winter -- to explore, lighthouses to snap selfies with, and orchards for picking some snacks when you're out of the water. If you're not into operating water vehicles yourself, take a ferry to Madeline Island or drive to it in winter, where there are plenty of hiking and bike trails. This is one of the most beautiful areas for fall colors, too, and peak color is reached around the second week of October. It peaks a little later here than inland, so plan your trip accordingly, and don't be concerned if you see too many brown leaves on your drive up.
Must-eat foods: Fried Lake Superior whitefish livers surrounded by flamingo decor at Maggie's; Cornish pasty and apple pie at Gourmet Garage; smoked trout crostini at Copper Trout.