Middletown, Delaware, located about 24 miles south of Wilmington, is an early crossroads town, one of the old Delaware towns not on a navigable waterway. It was originally a tavern stop about half-way on the old cart road that extends across the peninsula between Appoquinimink Creek in Odessa and Bohemia Landing on the eastern branch of the Bohemia River in Maryland; thus the name, “Middletown.”
Oxen pulled carts loaded with produce and materials between the ports of Cantwell’s Bridge (Odessa) and Bohemia Landing. This was the shortest route from the Atlantic Ocean to the Chesapeake Bay before the construction of the Chesapeake and Delaware Canal.
In 1675, Adam Peterson took on warrants for the land which later became the town of Middletown, the first survey being made in 1678. Later, his widow married David Witherspoon, a native of Londonderry, Ireland, and they settled upon the King’s Highway at the crossroads, first known as Mrs. Blackston’s Corner.
The Witherspoon’s Tavern was built at this site in 1762. A fire destroyed the upper portion of this building on Feb. 14, 1946, but the first floor remains. The cornerstone is still in the original part of the building.
Middletown was incorporated on Feb. 12, 1861. The first town council decided the town should be one mile square, commencing at the corner of the crossroads and extending one-half mile in each direction. Thus it was known as the “Diamond Town of the Diamond State.” As the town has grown, its boundaries have extended in each direction.
Among the oldest buildings in town is the Middletown Academy, erected in 1826. This was the former town hall on North Broad Street. It now houses the Middletown Area Chamber of Commerce and the Middletown Historical Society.
The memorial at Cochran Square – the “Four Corners” – was originally erected to honor the memory of men killed in World War I. Today, it honors all war heroes.