The town of Charles Town was established in 1742 by Act of the Maryland Assembly because, to quote the Act, “the encouragement of Trade and Navigation is the surest means of promoting the happiness and increasing the riches of every country . . . [and] . . . there being as yet no [town] settled at or near the head of the Chesapeake Bay . . .” The Assembly directed that “a place called Long Point on the west side of North East River in Cecil County” be the location of the new town and that it be named Charles Town in honor of the Right Honourable Charles, Lord Baron of Baltimore. A public wharf and a three-story warehouse were built. An inspector was appointed to ensure that only flour of superior quality was sold. And Charles Town was in business.

During the Revolutionary War, Charles Town was a major supply depot for the Continental Army. Two encounters with British warships are recorded. Early in the hostilities, a ship blockading the port was captured and its officers and men marched off through the streets of the town. In August 1777, the town was bombarded as a diversionary tactic while General Howe’s troops sailed up the Elk River to effect a landing.

When a severe hurricane in 1786 altered the ship channels in the Bay, making the ports of Baltimore and Havre de Grace more accessible, Charles Town’s prosperity began to falter. The following year, many distinguished Charles Town residents tore down their houses and moved to Baltimore in disgust when the town’s status as county seat was stripped away in favor of a town at the head of the Elk River—Elkton. Then, over the course of time, Charles Town slipped into obscurity, harmed by the long-term effects of the Revolutionary War and the advent of better roads that lessened traders’ dependence on water transportation.

Thus did Charlestown escape the more devastating aspects of “progress.” Its heritage is preserved in the Historic District, which includes approximately 175 buildings. None are mansions; most are the historic inns and amenities that served the populace during the busy colonial period. There are several Victorian buildings, but many structures that appear to be of late 19th-century or 20th-century origin are of a much earlier period, their true identities obscured by alterations applied over the decades.

Charlestown today is a small, water-oriented municipality with a population of about 1,000 people, four marinas, a general store, two restaurants, an elementary school, and a post office. The townspeople are content with it just the way it is.