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Route 153 connects two maritime towns in southern Connecticut: Westbrook (where the inventor of the first practical military submersible was born) and Essex (a major shipbuilding site 200 years ago, and one of the few American towns to be attacked by foreign warships).
In the 1920s, State Highway 153 followed today's Route 82.
The modern Route 153 was commissioned in 1932, with a symmetrically neighborly definition:
This differs from today's Route 153, which instead follows Plains Road to end at Saybrook Road closer to downtown Essex. The change was made on Jan. 2, 1967, as a result of the opening of the new Route 9 freeway. Plains Road, former SR 605, became part of Route 153. The old Route 153 segment along Westbrook Road became today's SR 604.