Set at the confluence of two branches of the tidal Westport River, the village has a rich architectural history from the late 18th century to the early 20th.

[1] The area that is now Westport, Massachusetts was originally part of neighboring Dartmouth, separating in 1787.

The point's potential for additional housing and maritime services resulted in significant development beginning around 1770.

The district extends linearly along Main Road for about a mile, ending roughly at Charles Street.

The most common architectural style found is the Greek Revival, whose height of fashion in the area was between 1835 and 1860.