LHD boundaries as described are approximate and subject to change. Consult the LHD Study Report on file with the relevant local district commission or municipal authority to verify district boundaries and whether a specific property, particularly one in proximity of a boundary line, is within the district. Also note that LHD boundaries may differ from those of State or National Register Districts.
The district includes buildings from a variety of architectural styles that range from the limited number of pre-revolutionary houses which survived the burning of the town by the British to and including a Romanesque library built in 1890 and a variety of Victorian residences. [NR]
Fairfield was originally laid out in four Squares, 25-30 acres each. Five streets were laid out, two running northeast-southwest, and three running northwest-southeast all the way to the beach. Newton Square contained the parsonage land for the use of the minister; Frost Square was, for the Meeting House, the Court House, the School House, and a third square, Burr Square was for a military or public park with a place for a burying ground, the fourth square contained land for the founder of the town, Roger Ludlowe. The Old Post Road historic district includes portions of these original four Squares. The Town Hall and the Town Green are the focal point of the original Four Squares.The first town house was built in 1720 and destroyed in 1779 by the British. It was rebuilt in 1794. At this time it had a five-bay front with central doorway topped by a hipped roof and a cupola. About 1870 the building was remodeled in the Second Empire style and in 1936 it was restored to its 1794 appearance which is recorded in a woodcut of that period. Since its restoration, hip roofed one-story wings have been added on either side to provide additional space. (see photograph) [NR]
Architecture, Education, Military, Political: The Old Post Road Historic District is significant because it is an impressive and aesthetically pleasing totality, and it is also significant from an historical point of view because it was the focal point of the first English settlement in the area and an important British target during the Revolutionary War. All of the buildings of the district taken together form a totality the richness of which eludes attempts at documentation, but which is comprised of the complex relationships of open and closed spaces and the counterpoint within and between differing architectural styles. After the conclusion of the Pequot war in 1637, Roger Ludlowe and a small group of Englishmen purchased a large expanse of land from the Indians which consisted of present day Fairfield, Greens Farms, Redding, Weston, Easton and the western section of Bridgeport. At that time the area was called Uncowaye meaning "looking forward - a valley", and at the time of settlement had belonged to the Pequonnock Indians. The Four Squares area which comprises the major part of the historic district was laid out immediately after the purchase of lands, and the earliest development of the town of Fairfield took place there.During the Revolutionary War, Fairfield became a British target in part because it was the center of whaleboat warfare along the sound. [NR]
 District information retrieved from the town website http://www.fairfieldct.org/.Final report, Historic District Study Committee, Fairfield, 1963, Reprinted 1969, Fairfield Museum and History Center, Fairfield.  Assessors information retrieved from the website www.visionappraisal.com.[NR] Constance Luyster, Fairfield Historic District, National Register Nomination Number- 71000897 NRIS, National Park Service, 1971 - http://pdfhost.focus.nps.gov/docs/NRHP/Text/71000897.pdf; http://pdfhost.focus.nps.gov/docs/NRHP/Photos/71000897.pdf.
The list of the properties and the parcel IDs has been obtained from the final report, Historic District Study Committee, Fairfield, 1963, Reprinted 1969, Fairfield Museum and History Center, Fairfield.  The district also includes at least eight other properties for which only the owner name and contact address has been provided in the report, without the street address nor the parcel IDs.