Route 153 begins as Essex Road in downtown Westbrook, at an intersection with US 1.

It heads north, passing by the Westbrook railroad station and the access road to the Tanger Outlet Mall, before intersecting with Interstate 95 (I-95) at Exit 65 about half a mile north of US 1.

Route 153 continues northeast towards Essex Village along Plains Road; Westbrook Road continues north as an unsigned state highway (designated as State Road 604) towards the village of Centerbrook.

When first created, the northern end of Route 153 ran along Westbrook Road like the old highway.

In January 1967, the northern end was rerouted to its current location to accommodate an interchange with the Route 9 freeway.