This area includes the best-preserved and most architecturally interesting commercial buildings of the city's mid-to-late 19th century development, when it was the leading port on Penobscot Bay.

In the second half of the 19th century it was served by steamship service to other ports, and was connected by railroad to Boston and Portland.

The city's downtown is organized as a series of roads paralleling the southern bank of the river, which is oriented roughly northwest to southeast.

Notable early buildings include the Waldo County Courthouse (1853) and City Block (1850), both designed by Bangor architect Benjamin S. Deane, and the 1855 Customhouse and Post Office, designed by Ammi B.

Notable later buildings include the Masonic Temple, which occupies a prominent position on the Church Street intersection, and the Belfast National Bank, both built in the late 1870s to designs by George M. Harding of Portland.