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Ellicott City, MD
Ellicott City was founded in 1772 by Quaker brothers John, Andrew, and Joseph Ellicott, who built flour mills along the Patapsco River, and the town grew around that milling industry into a substantial 18th- and 19th-century commercial center whose historic Main Street, built directly into the steep river valley, remains one of the best-preserved collections of colonial and Federal-era architecture in Maryland. The B&O Railroad's Ellicott City Station, built in 1830, is recognized as the oldest surviving railroad station in the United States, and it's preserved today as a museum documenting the town's foundational role in early American railroad history. The town's low-lying position directly along the Patapsco River has also made it repeatedly vulnerable to severe flash flooding, including two devastating floods in 2016 and 2018 that destroyed numerous historic Main Street businesses within just two years of each other, prompting significant public debate and infrastructure investment around flood mitigation for the historic district. Ellicott City's combination of nationally significant early railroad history, exceptionally well-preserved 18th- and 19th-century architecture, and its ongoing, serious flooding vulnerability has made it one of the most historically rich and most closely watched small towns anywhere in the greater Baltimore area.
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Annapolis, MD
Annapolis has served as the capital of Maryland since 1695 and briefly functioned as the capital of the entire United States in 1783 and 1784, when the Continental Congress met in the Maryland State House — the building where George Washington formally resigned his military commission, an event now considered one of the more remarkable voluntary transfers of power in the founding of American democracy. The United States Naval Academy, founded in Annapolis in 1845, occupies a substantial waterfront campus along the Severn River and gives the city an enduring military-academic identity, with the Naval Academy's massed formations, sailing programs, and graduation ceremonies drawing visitors well beyond the school's own midshipmen and their families. Annapolis's historic district, built around a colonial-era street grid radiating out from the State House and the Naval Academy, has preserved one of the highest concentrations of original 18th-century buildings still standing in any American city, a density of colonial architecture that's made the compact downtown a genuine open-air museum. Annapolis's combination of serving as Maryland's colonial-era and current state capital, briefly hosting the entire nation's capital function, and housing the US Naval Academy has made it one of the most historically significant small cities anywhere on the East Coast, sitting at the edge of the greater Baltimore-Washington corridor.
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