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.
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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.