Charlestown was built in a protected area on the Leeward side of Nevis, situated between Fort Charles and the Fort Black Rocks. Most of the original buildings were destroyed over time by earthquakes, leading to the common practice of building a series of wooden upper floors over a stone ground floor.

The city was the birthplace of Alexander Hamilton, and is the site of the oldest synagogue in the Caribbean. During the 17th century many Sephardic Jews came to Nevis and the Antilles after being expelled from Brazil.