The Harpswell Inn was built in 1761 and was originally known as the Summer House, which it served as for the Curtis family. Following that, it became the the Lookout Point House and primarily served as the cookhouse for the Lookout Point Shipyard. The shipyard flourished around the Civil War, and for about twenty years schooners and brigs ranging from 20 to 200 tons were built and launched there. Sometimes there were as many as four vessels being built at once.

The foremost remaining symbol of the inn’s connection to the shipyard is the bell a-top Harpswell Inn, which in the 1860s summoned the shipbuilders to their meals.