Galena, IllinoisStock 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.
York, PennsylvaniaCourtesy Downtown inc
Known as the White Rose City, York has seen a revitalized main street in the past few decades. Market Street is filled with local businesses setting up shop in Victorian and Classical Revival style buildings, and on the first Friday of each month, the shops stay open late to bring visitors together. One of the major attractions on Market Street is the Central Market, which has been in business since 1754.
Ridgewood, New JerseyDH.Lee/Shutterstock
Within the family-friendly neighborhood, Ridgewood’s main street is densely packed with a movie theater and numerous boutique shops and restaurants. East Ridgewood Avenue is the main artery, connecting the downtown historic district to modern accommodations. Some standout structures are the late-18th-century Archibald-Vroom House—the oldest building in the village—and the sprawling California Mission Revival-style train station, where commuters can get into midtown Manhattan within an hour. The train station dates back to 1916 and is listed on the national and state Register of Historic Places.