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Hagerstown earned the nickname Hub City in the 19th century because five major railroad lines converged here in western Maryland, making it one of the most important rail junctions between Baltimore and Pittsburgh. Jonathan Hager, a German immigrant, built a stone house and trading post here in 1739 at the confluence of several Native American and colonial trading paths, and the grid he laid out became one of the earliest planned towns west of the Appalachians. That house, preserved as the Hager House and Museum on Key Street, is the oldest structure in the region and gives the city a starting point for understanding three centuries of Appalachian border history.

Hagerstown sits in the Cumberland Valley, and within ten miles lies more significant Civil War ground than almost any other city in Maryland.

Antietam National Battlefield at Sharpsburg, site of the bloodiest single day in American history on September 17, 1862, is 12 miles south, while South Mountain State Battlefield and the preserved iron furnace at Gathland State Park document the campaign that preceded Antietam by two days. The Washington County Museum of Fine Arts in City Park holds a collection of 19th-century American paintings that is genuinely impressive for a city of this size, donated largely by the Museum's founders William Henry and Anna Brugh Singer in 1931.