Unusual in Delaware for having been founded away from any navigable river, Middletown coalesced at an early crossroads, a tavern stop at the “middle” of the Delmarva Peninsula, halfway between landings on the Appoquinimink River on the east and the Bohemia River, Maryland, on the west. Its present appearance is largely late nineteenth century and later, as the place experienced rapid growth after the railroad came through in 1855. Peach farming on the fertile “Levels” brought prosperity. Cass and Broad streets have sizeable nineteenth-century houses, and the mid-nineteenth-century brick Italianate house at 123 W. Main St. sports an ornate cast-iron porch, a feature somewhat uncommon in the state. Wilmington contractor John A. Bader kept a minute record (now at the Hagley Museum) of the construction of Middletown Theater on Main Street (1922), now the Everett Theater, where a venerable carbon-arc movie projector is still operational. At the town center is a small civic plaza by a New York designer (1980, Ben-Ami Friedman and Associates).
The adjacent Witherspoon Building contains parts of a tavern built in 1761 that survived a fire in 1946. Starting in the 1990s, Middletown's population exploded, and the town's acreage was tripled. Among many new buildings is the Volunteer Hose Company (1999, Richard Conway Meyer and Lawrence D. McEwen). A recently printed walking tour by the Downtown Revitalization Office discusses forty-five historically significant structures in town.
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