The area was settled in June 1783 by the United Empire Loyalists under the leadership of Sir Robert Dig by.
The town developed a sizable shipping fleet in the 19th century. One famous Dig by vessel was the brigantine Dei Gratia, which discovered the famous mystery ship Mary Celeste in 1872. The town became an important regional transportation centre in the 1890s with the arrival of the Dominion Atlantic Railway. Trains connected with a series of steamships such as the City of Monticello and later the SS Princess Helene.
The town's history is preserved and interpreted by the Admiral Dig by Museum, located in a historic home facing the harbour
