Chesapeake City, Maryland, located 60 mi/95 km northeast of Baltimore, is one of the Upper Bay's most appealing towns. It is nestled under the arching span of the Chesapeake City Bridge along the Chesapeake & Delaware Canal.
The tree-shaded streets of Chesapeake City's historic district are lined with renovated, brightly painted houses from the 1800s—many of them originally canal workers' homes that have been converted into shops and restaurants. The Blue Max (1854), a bed-and-breakfast, was once owned by Jack Hunter, who named the building after his most famous novel.
Stop by the Chesapeake & Delaware Canal Museum to see artifacts and displays about the canal's history. For a good look at how the waterway works, sit in one of the canal-side restaurants and watch huge international vessels glide silently through, dwarfing the buildings.
South of town is some of Maryland's prettiest horse country—more than 800 Thoroughbreds live on well-manicured farms with level green pastures enclosed by miles/kilometers of neat brown fences. Racing superhero Kelso lived and died there, at Woodstock Farm, which is owned by the du Pont family. Tours are available.
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