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In 1650, Middletown earned its name due to its location, halfway between the mouth of the Connecticut River and the first Connecticut settlement of Windsor.

Growing from a key Native American village into a colonial one, then into a major seaport, Middletown eventually became the wealthiest town in Connecticut by the mid-1700s. In the early 1800s, although international disputes adversely affected Middletown's seafaring trade, manufacturing prospered. Factories turned out everything from ship hardware and textiles to sleigh bells and sidearms for Union army officers. Trolleys encouraged suburban expansion while railroads, and later highways, greatly influenced commercial development, while many immigrants from Europe made Middletown their home around the turn-of-the-century. Today, Middletown is perhaps best-known as the location of Wesleyan University, one of the "Little Three" liberal arts colleges.