Incorporated in 1784 but settled by Europeans approximately 150 years earlier, Middletown was initially a settlement based on agriculture and the port that developed along the Connecticut River. The city grew prosperous on a foundation of trade with the West Indies and the produce of farms wrested from the hills and forests.
While the majority of Middletown voters in the 1860 election were Democrats, the Republican party took advantage of their rival’s divisions, and campaigned hard to ensure Lincoln's victory. South Carolina seceded from the Union on December 20, 1860, swiftly followed by the other Southern states. The bombardment of Fort Sumter on April 1861 marked the beginning of armed hostilities between the United States of American and the Confederate States of America.