A small-town getaway, Cedarburg is about 20 miles north of Milwaukee and offers visitors a chance to walk down the main street and pop in and out of shops, inns, cafes, and art galleries and museums—many of which are nestled inside historic buildings.
Frederick is the third-largest city in Maryland and its views of the Blue Ridge Mountains are one of the major attractions. The beautiful main avenue, Market Street, is another. The hip-meets-historic vibe of the main street features churches and shops like The North Market Pop Shop, which sells 400 types of vintage sodas.
Conforming to the shape of the Galena River, Galena’s Main Street offers visitors access to a riverfront walkway. The architecture is in the Italianate style, with brick storefronts and bay windows. Trolley cars bring visitors and locals alike to nearby wineries. A three-hour drive from Chicago, Galena is a great place for a riverside journey, especially at the DeSoto House Hotel, which has hosted guests like Ulysses S. Grant since 1855. Check out the funniest street names in every state.