James Meyer/Shutterstock 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.
Jon Bilous/Shutterstock 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.
Stock Connection/Shutterstock 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.