On Minnesota's North Shore of Lake Superior, this village of 1,400 is more cosmopolitan than many towns 20 times its size it has a performing-arts center, a folk school, an art colony and galleries and restaurants that could hold their own in much bigger cities.
Details: For more, see Four seasons of Grand Marais.
The downtown Minneapolis riverfront is a magnet for tourists and locals alike, and everyone wants to be outdoors: listening to free concerts, dining at sidewalk tables and strolling on the Stone Arch Bridge.
What to do: Run, walk, bike or skate along the riverfront. Tour the Guthrie Theater. Take a historic walking tour from Mill City Museum. Go to the Mill City Farmers Market on Saturdays. See free water-ski shows on Thursdays.
Details: See On the river in Minneapolis.
In summer, everyone wants to be in Chicago, and the price of hotel rooms skyrockets. But the entertainment is free once you get there, and it's easy to eat well for very little.
Where to stay: See Where to stay in Chicago.
In summer, this hamlet in Minnesota's southeast corner kicks into high gear as bicyclists, paddlers and trout fishermen stream into its many inns and B&Bs.
The beautiful Root River State Trail jump-started Lanesboro's renaissance in the 1980s, but now tourists also come for the theater and art.
Details: For more, see The belle of bluff country.
In the southeast corner of Wisconsin, Lake Geneva has been welcoming wealthy Chicagoans for 150 years. They came, they built fabulous mansions, and now the rest of us get to gawk at them from a footpath that hugs all 20 miles of shoreline.
When to go: Now, when it's still fairly quiet. July and August are crowded, especially on weekends.
What to do: Walk around Geneva Lake; if you want to walk only the eight miles from Lake Geneva, an excursion boat will pick you up in Williams Bay. Shop downtown. Rent a kayak, canoe or stand-up paddleboard. Swim at the municipal beach or rent a motorboat.
Details: For more, see Gawking in Lake Geneva.