Chaptico may be Algonquian for "big-broad-river-it-is" and related to the friendly Chaptico tribe visited by Gov. Charles Calvert in 1663. The town was a shipping point until the Wicomico River silted up in the 18th century. It was damaged by the British in 1813, during the War of 1812. Some of its prominent citizens were pro-Southern and jailed during the Civil War.
Chaptico has a number of properties listed on the National Register of Historic Places, including Bachelor's Hope, Christ Episcopal Church, and Deep Falls. Nearby are Maryland International Raceway, Budds Creek Raceway, and the golf course community of Wicomico Shores.
- U.S. Geological Survey Geographic Names Information System: Chaptico, Maryland
- Arnett, Earl, Brugger, Robert J., and Edward C. Papenfuse Maryland: A New Guide to the Old Line State (2nd ed.) The Johns Hopkins University Press, Baltimore 1999 p. 9.
- Zilliox, Jackie (Summer 2007). "Chaptico's Encounter in the War of 1812". somd.com. Southern Maryland This Is Living magazine. Retrieved 2009-06-02.
- National Park Service (2008-04-15). "National Register Information System". National Register of Historic Places. National Park Service.
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