Essex is one of the few American towns to ever be attacked by a foreign power; this occurred on April 8, 1814, and the economic losses were among the largest sustained by the United States during the War of 1812. 28 vessels, with a total value estimated to be close to $200,000 (at a time when a very large two story home in Essex, then known as Potapoug Point, would have been worth no more than $1,000), were destroyed by the British. One historian has called it the "Pearl Harbor" of that war.

On that date, approximately 136 British marines and sailors under the command of Richard Coote (or Coot) rowed 6 boats from four British warships (the Hogue, Endymion, Maidstone and Borer) anchored in Long Island Sound, 6 miles up the Connecticut River, past the unmanned fort in Old Saybrook, arriving at the boat launch at the foot of Main Street in Essex close to 4 A.M. The boats were armed with swivel guns loaded with grapeshot, the officers armed with swords and pistols, the marines with "Brown Bess" muskets, and the sailors with torches and axes; they responded to the single cannon fired by the town's surprised defenders with a massive volley, neither side incurring any casualties. They quickly commandeered the town, eliciting a promise of no resistance from the Essex militia in return for promising not to harm the townspeople or burn their homes, while a messenger rode to Fort Trumbull in New London for help. A dubious local myth states that Coote did not burn the town as a favor to a local merchant who greeted him with a secret Masonic handshake.

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