Boothbay Harbor has been an important fishing ground since 1666, when Europeans used it as a seasonal fishing location. In 1730, the area was settled and the harbor was named Townshend Harbor until 1843 when it was renamed as Boothbay Harbor.

Boothbay continued to develop as a fishing center through the 19th and 20th centuries. In 1889 Boothbay Harbor broke from Boothbay, becoming its own town.

During the revolutionary war Boothbay Harbor was used as a meeting place for the American naval fleet and then again in World War II Boothbay Harbor aided the war effort by building minesweepers for the navy.

Though still a working waterfront, Boothbay Harbor has become a popular tourist and leisure sailing destination.

The Tichnor Brothers printing company published this type of postcard circa 1938 as part of their Maine series. These, and other postcards, by the Tichnor Brothers Company are officially known as the Tichnor Gloss Series because the photographs were notoriously retouched on such a level that does not allow the postcards to be classified as photographs or paintings. The caption reads, "Squirrel Island & entrance to Boothbay Harbor, Me."