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The historic town of St Michaels dates back to the mid-1600s when it served as a trading post for area tobacco farmers and trappers. In 1672 the Christ Episcopal Church of St Michael Archangel parish was founded in present day St. Michaels and established the name of the town as 'St Michaels'. In 1778 a British land agent, James Braddock, purchased 20 acres and deeded 58 lots. This created St. Mary's Square, the historic center of St. Michaels.
In the early days of the town, St. Michaels became predominantly Methodist following visits by itinerant Methodist preachers. Braddock donated land for a Methodist church in the center of St. Mary's square, and a brick structure built as the Sardis Chapel remains on that site.The town's earliest industry was shipbuilding, and as many as six shipbuilders were active in or near the town by the War of 1812. Their typical product was a fast schooner, a type later known as the Baltimore clipper. Such vessels were capable of evading blockades and outrunning pirates or foreign naval vessels at sea, and some were later used as private armed vessels carrying a letter or marque. For example, Thomas L. Haddaway launched the schooner Lottery at St. Michaels in 1812, and her owners obtained a letter of marque and reprisal. A letter of marque and reprisal was a government license authorizing a person (known as a privateer) to attack and capture enemy vessels and bring them before admiralty courts for condemnation and sale. Cruising for prizes with a letter of marque was considered an honorable calling combining patriotism and profit, in contrast to unlicensed piracy, which was universally reviled.
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The town played a role in the War of 1812 when, in 1813, a fleet under the command of Admiral George Cockburn moved up the Chesapeake Bay, and targeted St. Michaels because of the presence of a militia battery erected to defend the town and its shipyards. Under cover of early morning darkness on August 10, 1813, the Battle of St. Michaels commenced as the British sent a landing party ashore just south of the town, and after a brief exchange, neutralized the battery and returned to their boats. The British proceeded to bombard the town from the barges and a brig, but failed to destroy the shipyards or cause any substantial damage to the town. The militia returned fire from artillery batteries at Impy Dawson's wharf (the foot of Mulberry Street) and Mill Point (the foot of Carpenter Street). A contemporary report noted that 'several houses were pierced' by the British fire. Nearly a century later a story was recorded that as a result of the town's ruse of dimming the lights and hanging lanterns in the trees beyond the town, the town was spared. Based on this story, St. Michaels became known as 'the town that fooled the British,' a nickname selected during the sesquicentennial celebration of the battle in 1963. The Cannonball House survives as one of the structures reportedly struck by one of the shots, and is on the National Register of Historic Places, as is the Saint Michaels Historic District.
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Shipbuilding declined after the War of 1812, but an oyster industry revived the town a few decades later. By the late nineteenth century, most households in the town had at least one person engaged in some aspect of this fishery, either tonging oysters from the nearby waters of the Miles River and Eastern Bay, or engaged in the shucking houses that came to line the waterfront. One of these businesses, Coulbourne and Jewett, founded in the early years of the twentieth century, is notable as a black-owned enterprise, and it early came to specialize in crabmeat. As a means of marketing crabmeat, owner Frederick Jewett devised a five level grading system (regular, claw, special, backfin, lump) which is still used by the industry today. Pictured to the right are Mr. & Mrs. Jewett.
