Why it’s so great: Galena’s charm makes it the best small town in Illinois all year round, but it’s especially great in summer, when you can ride the free trolley to go bar- and restaurant-hopping down the quaint Main Street. Plus, there’s a bunch of fun activities to be found along the Galena River, such as kayak and canoe rentals and riverboat cruises. Or just pick up some vino from one of three area wineries and spread out a blanket along the scenic Galena River Trail.
Where to eat and drink: If you’re lucky enough to be here on the Fourth of July, grab burgers and brats while chatting up friendly locals at the annual rooftop party atop the historic DeSoto House, the oldest hotel in Illinois. The Goldmoor Inn, perched high on a bluff overlooking the Mississippi, is never a bad idea for romantic fine dining, and Vinny Vanucchi’s downtown is a fun locals spot for casual Italian.