The Fairfield Historic District [†] was listed on the National Register of Historic Places in 1971.
Fairfield was originally laid out in four Squares with about 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 Fairfield Historic District includes portions of the original four Squares. It includes all buildings bordering the Old Post Road from the Post Road to Turner Street and it includes the buildings southeast and northeast of the Town Hall on both sides of Beach Road to a point just before the Old Burying Ground which is on the southwest side of Beach Road and is included in the Fairfield Historic District. The total area of the Fairfield Historic District is about 35 acres.
Historically and Architecturally Interesting Buildings of the Fairfield Historical District
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.
No. 1 Town Hall Green, "Rising Sun Tavern" — Built in 1780 by Samuel Penfield, this tavern sheltered some prominent visitors in the post-revolutionary period from 1780 to 1818. It is a gambrel roofed building with five bays and additions, include wings to the side and the rear, the porch, chimneys and dormer windows.
543 Old Post Road, The Silliman House — This building was built in 1791 by Major William Silliman, son of General Gold Sellect Silliman who was in charge of the troops guarding Fairfield in 1779. It has a two-chimney central hallway plan and an elaborate porch with a flared curved roof supported by slender columns. There are additions to the side and rear of the house.
The Fairfield Academy, which became known as the Old Academy, has been moved from its original site to its present position southeast of city hall. It is distinguished by a cupola on the roof and by small circular windows in the gables as well as by a dominant gabled section which projects somewhat from the facade.
249 Beach Road — This house has a central chimney plan with later additions to the rear and side. It survived the British raid of 1779 because a servant hiding in the house put out the fire. It is owned by the Misses Emily and Catherine Porter.
303 Beach Road — This center chimney colonial house was originally a salt-box. At the time of the burning of the town by the British, Mrs. Jonathan Bulkley whose brother piloted the landing of the British forces is believed to have arranged that the houses on Beach Road be spared. When this was learned, returning colonial troops believing her a Tory threatened for a while to destroy her and her house. The house is now  occupied by Mr. and Mrs, Samuel Glover.
349 Beach Road — This is one of the few examples of a salt-box in the Fairfield Historic District. It was built prior to 1750. It is now owned by Mrs. C.G. Williams.
739 Old Post Road — The Burr Mansion is located southwest of the Town Hall and the Town Green to the rear of the Old Academy. It is a building which was built in 1740 as a two-chimney colonial with a wide center hall. The building was adapted to the Greek Revival style in 1840. The roof was raised and a two story portico was added in the front, the roof of which is framed into the house just below the frieze which is plain. There are eyebrow windows in the frieze to admit light to the third story. The mansion has a long history of association with eminent persons including President Dwight of Yale and the artists John Trumbull and John Singleton Copley. It is now owned by the town of Fairfield and is used for town offices.
952 Old Post Road — Built about 1750 this house is located on the Old Post Road around the corner from the Burr Mansion. It is an example of the smaller houses erected at that time. It was the homestead of Andrew Rowland and was spared in the burning of Fairfield in 1779.
The Fairfield Historic District includes approximately 75 buildings in a variety of architectural styles. These 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. All of the buildings 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. Thus the Fairfield 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.
After the conclusion of the Pequot war in 1637 when the area appeared secure from further Indian warfare, 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 Fairfield 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. In July of 1779 General Tryon attacked the town and in two days Hessians burned two hundred houses and all public buildings. When Washington passed through the town on his presidential tour in 1789 he recorded in his diary that "The Destructive evidences of British cruelty are yet visible both in Norwalk and Fairfield."
F.S.M. Crofut. Guide to the History and the Historic Sites of Connecticut. New Haven: Yale University Press, 1937.
Fairfield, Conn: 1639-1964. Booklet published by the town of Fairfield on the three hundred and twenty-fifth anniversary of the founding of Fairfield.
‡ Adapted from Constance Luyster, Connecticut Historical Commission, Greenfield Hill Historic District, Fairfield, Connecticut. nomination document, 1970, National Park Service, National Register of Historic Places, Washington, D.C.
Beach Road • Belmont Street • Benson Road South • Old Post Road • Post Road