Introduction: By the 1800’s, the era of international trade for Kent County was over. Baltimore was now the hub for shipping wheat and other products abroad. Kent’s early transition to wheat and grains, and innovations in farming techniques reinvigorated the economy and attracted newcomers such as George Burgin Westcott, who purchased the Geddes-Piper house in 1836. “Wheat is in demand…and looking up. You may calculate on an advance price…except something unfavorable should take place abroad,” wrote William R. Stuart, a Baltimore merchant, to Joseph Wickes of Chestertown on November 13, 1829. Nevertheless, Kent County and the Eastern Short were in a period of political transition. Wealthy landowners no longer dominated local politics on the upper shore, and a rising class of small farmers, merchants, artisans and laborers sought their own place in government. These tensions came to a head during the War of 1812, but continued through the years leading up to the Civil War.

War of 1812: Baltimore emerged as one of the top commercial cities in the United States in the late 1700s thanks to the productive agricultural lands throughout Maryland. But by 1807, the economic tensions with Great Britain that fueled the American Revolution flared again. Great Britain refused to recognize America as a neutral party in the European war, which led the States to declare an economic boycott that was especially devastating to wealthy farmers. This landed gentry, along with merchants and bankers, dominated the Federalist Party, which opposed the embargo and the war declared in 1812. In Kent County, the more egalitarian Republican Party made up of small farmers and merchants, artisans and laborers had risen in popularity after the war, but citizens dreaded the risks of a new war. Anxiety over skirmishes and the bombardment of Fort McHenry in Baltimore brought the anti-war Federalists temporary support, but in the end, American victory in the War of 1812 meant victory for the more “democratic” Republicans.

The threat along the Chesapeake Bay was very real. By 1813, a British blockade had nearly closed the Bay and ships constantly threatened farms and towns. In May 1813, the British were positioned at the mouth of the Sassafras River and sent a detachment of about 500 men to burn Georgetown and Fredericktown. After burning the lower part of the town, the British set fire to a brick house at the top of the hill when a woman named Catherine (“Kitty”) Knight implored them not to burn the house as there was an old woman ill inside. Kitty Knight kept protesting as the men proceeded to the next house, until finally they left. The heroic Kitty put the fires out and saved the structures that would later be known by her name.

The burning of the Capitol in Washington in August 1814 sent a wave of anxiety along both shores. Seven miles west of Chestertown, the 21st Maryland Militia under Colonel Phillip Reed was encamped near Fairlee when news reached them that a British frigate and two smaller vessels were headed toward them. British captain, Sir Peter Parker, had been ordered to prevent the militias from crossing the Bay to defend Baltimore. On August 28th, Parker landed 100 men near the mouth of Fairlee Creek and burned every building on the farm of John Waltham, the wheat in his granary and the stacks in his field. Two days later, they burned Richard Frisby’s farm and made plans to capture Colonel Reed and his men. Instead Colonel Reed learned of surprise attack and was waiting when they arrived. The two sides met in a field belonging to Isaac Caulk. Despite being outnumbered and running out of ammunition, the Americans pushed back Parker’s men until they retreated. Over forty British were killed or wounded, with Parker among the dead.

19th Century Businesses: Although international trade declined in Kent, thriving mercantile establishments rose in Chestertown to serve the surrounding area. Thomas Eliason, Abel Reese, B.B. Perkins, Thomas Hynson, and William Albert Vickers were among those who advertised clothing, dry goods, groceries, hardware, and farming implements in the mid 19th century. Ladies such as Mary Perkins and Eliza Smith ran millinery shops.

African American businessmen and women also prospered: Levi Rogers operated an ice cream saloon, serving oysters and terrapins in season. William Perkins owned the Rising Sun Saloon, with an “oyster room” for men only, and the “east room” for ladies and their gentlemen guests. James Jones earned a reputation for high quality roasts at his grocery and butcher shop. Maria Bracker owned a restaurant offering customers sponge cakes, ice cream, and lemonade.