Winona
Winona's renewal started with the founding of the Great River Shakespeare Festival (www.grsf.org), which runs from the end of June to the end of July and features Equity actors from New York and Los Angeles. The city has since added the new Minnesota Marine Art Museum (www.minnesotamarineart.org), with exhibits of folk art, historical river photographs, and a fine rotating collection of 19th-century maritime paintings by the likes of Winslow Homer. Winona also hosts the Minnesota Beethoven Festival in the summer and now has a wintertime Frozen River Film Festival. And if you need a bite to eat, the Blue Heron Coffeehouse features tasty organic fare as well as live acoustic jazz and bluegrass music several nights of the month.

Lanesboro
From Winona, you might take a side trip along one of the Mississippi's cultural tributaries. Keep going south on Highway 61 about 45 minutes until you come to Highway 16, then turn west and drive another hour to Lanesboro, Minnesota, a town on the Root River that's regularly chosen as one of the best small art communities in the country. This is mainly due to the visual arts community and the Commonweal Theatre (www.commonwealtheatre.org), which was founded in 1989. While you're in town, you can either sit down for a prix-fixe menu of French cuisine at the Vintage, or just grab a bratwurst and cold beer and dance to polka music at the old-school Das Wurst Haus.

National Mississippi River Museum and Aquarium
When you get back to the river, turn south on Highway 26. A 90-minute drive will bring you to Effigy Mounds National Monument, where you can walk among 4,000-year-old effigies of birds and bears left behind by prehistoric Native Americans. Then continue south along the county roads that hug the river until you reach Dubuque, Iowa, where a different kind of museum opens a window onto the river itself. The National Mississippi River Museum and Aquarium (www.mississippirivermuseum.com) is housed in an old shipbuilding factory, where you can watch giant catfish lumber around their tanks or take a cinematic, high-definition "Mississippi Journey" that offers a multisensory experience of traveling in a boat on the river.