This document is a tour guide to the historical features of the seaports of Black Rock and Southport in the town of Fairfield, Connecticut. It is designed to acquaint visitors and residents with the stages of development that shaped both ports and the way that Fairfield has evolved through wars, depressions, and periods of prosperity over the centuries. From Black Rock and Southport, both natural harbors, goods and produce were shipped in early colonial days. Black Rock was a major West Indies trading port and shipbuilding center, while Southport was the base for a market fleet and a residence for wealthy shipowners. Later, during the Victorian era, these areas became summer resorts, and still later became mostly residential communities. The history of Black Rock is traced from its beginning in 1644 through the hey-days of its West Indies trade, 1760 to 1815. Its declining period between 1865 and 1900 is discussed, followed by a report of the port's evolution into a residential community during the 20th century. Southport contains some of the finest architecture and streetscapes design produced in early America. From its beginnings Southport had a simple village atmosphere, mainly due to its residents' successful prevention of the development of a manufacturing economy. The history of Southport is traced from its origins as a farm community in 1661 through 1800. From 1800 to 1854 it was a center for coast trading, and then gradually evolved more and more to a residential area. Throughout the document existing historical landmarks are noted. The document also contains numerous maps and photographs. (BC)