Though much smaller than New Castle, Odessa possesses one of the finest collections of late 18th- and early 19th-century architecture in the middle-Atlantic region. The center of town is now on the National Register of Historic Places, and local authorities have zoned the entire town as historic.

For the first 134 years after its founding in 1721, the town was known as Cantwell’s Bridge, named after an early toll bridge across the Appoquinimink operated by a son of Captain Edmund Cantwell, who gained title to the area in 1664. Throughout the 18th century, the village grew in importance as a port for wheat, corn, tobacco, and other products produced on the large inland plantations of the upper peninsula.

Odessa enjoyed its greatest wealth and prominence from the last decades of the 1700’s through the 1840’s. The decline of the peach crop, which fell to a peach blight, as well as the railroad passing through Middletown rather than Odessa both played a role in the decline of the town.

Odessa was given its present name in 1855 when town fathers, concerned by the decline of the town’s former prominence as a shipping point for grain, renamed it for the Black Sea grain port in an apparent effort to shore up its sagging economy. The officials of the village of Duck Creek Crossroads, a few miles south, adopted a similar strategy by renaming their town Smyrna. In neither case was the renaming successful in meeting its goal; however, the new names have lasted.

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