America's Greatest Main Streets
Galena’s Main Street bends gently as it follows the Galena River (a tributary of the Mississippi) and presents a medley of brick storefronts and bayfront windows, many in an Italianate style. This is the home turf for chocolate shops and galleries—and the second home of many Chicagoans who escape the Windy City three hours away. Trolley cars depart from Main Street for area wineries, and at the intersection with Water Street, you can turn onto a riverfront walkway.
Worth a Stop: DeSoto House Hotel has welcomed prominent guests since 1855. Locals flock here, too, for events such as a trivia quiz night in honor of Ulysses S. Grant’s birthday.