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High Street and Wesleyan University (founded in 1831) share a fascinating, intertwined history. From this major inland port on the Connecticut River, Middletown's sea captains and merchants made fortunes in the 18th and early 19th centuries trading with the West Indies, South America, and China. Others enjoyed wealth amassed from the local manufacture of swords, firearms, and marine hardware. These prominent families built fashionable villas of the latest architectural designs on High Street. Many of their homes remain, and two have been designated national historic landmarks. With spectacular views of the river valley below, its avenue of arching elms, and the addition of Wesleyan's formidable "Brownstone Row," the street has attracted many to the hill. Dignitaries, including George Washington, the Marquis de Lafayette, William Howard Taft, and Martin Luther King Jr., came to High Street.

The predecessor of the US Coast Guard (USCG) was the Revenue Marine, formed to enforce the customs laws. The officers for the service were drawn from the Merchant Marines, and occasionally the US Navy, and political connections were often more important than competency. To ensure consistent training, the original Revenue Cutter School of Instruction became the US Coast Guard Academy, moving to its present location in New London, Connecticut, in 1932. Prior to that, instruction had been afloat on four different vessels, known as cutters, and ashore in New Bedford, Massachusetts; Curtis Bay, Maryland; and Fort Trumbull in New London. The training has grown from a two-year program, providing primarily practical seamanship, to one of the highest ranked small engineering undergraduate schools in the nation, offering nine majors and graduating male and female officers with a liking for the sea and its lore.