Home | Whats New | Site Index | Search

Boston Post Road Historic District

Darien Town, Fairfield County, CT

The Boston Post Road Historic District was listed on the National Register of Historic Places in 1982. Portions of the content on this web page were adapted from a copy of the original nomination document. []


The Boston Post Road National Register Historic District in Darien, Connecticut, runs along a block and a half of the Post Road from the Town Hall, on the west to the Congregational Church and houses associated with it on the east. Twelve 19th century houses, the only remaining such group along the Post Road in Darien, occupy the central section of the Boston Post Road Historic District.

The Boston Post Road Historic District embraces approximately 26 structures on approximately 1.7 acres of land. Three structures are considered not to contribute to the historic character of the district.

The area of the Town of Darien that surrounds the Boston Post Road Historic District includes the main business street, the Connecticut Turnpike, a shopping plaza, modest houses and a number of large houses. The area is a mix typical of Fairfield County, on the fringe of the greater metropolitan New York City region and within commuting distance of the city. In recent years, new construction on the Boston Post Road in the vicinity of the district has included a convalescent home and an office building.

The symbolic pivot of the Boston Post Road National Register Historic District is the red brick, Greek Revival style edifice of the First Congregational Church of Darien (successor to the Middlesex Ecclesiastical Society) at 14 Brookside Road, constructed in 1837. The Doric columns of its tetrastyle portico rise from a modern, flagstone stylobate to a pediment with tympanum of flush horizontal boards. The entablature and raking cornices are plain, without moldings. The central, double, panelled doors are flanked by similar single doors, while above the three doors there are three 12-over-12 windows. The brick is laid up in common bond with grey mortar. Each side wall has five 12-over-12 windows; the fifth bay was added when the church was enlarged in 1860. There is a short, square wood tower whose front wall is in the same plane as the facade of the building. Each corner of the tower has a spirelet.

The interior of the church, relatively plain, is dominated by the galleries on three sides. The front wall is given over to gold-colored organ pipes.

Twentieth-century construction activity has included two large additions to the church. The first, c.1925, abutting the earlier structure, is one-story high, built of red brick with red mortar and with white wood trim in a "colonial" effect dominated by a large bow of five 12-over-12 windows on the east elevation. The second large addition, built after mid-century, is a separate structure connected by a glass corridor to the first addition. While the materials of the second addition are red brick and white trim, the flat roof, solid brick walls and glass entrance are in a contemporary mode executed in scale and mass sensitive to the rest of the complex.

The Town Hall at 719 Boston Post Road was built in 1910 as a school. The dominating feature of this 2-1/2-story, Neoclassical Revival, brick block is its roof. The roof is hipped, with oblong chimneys, dormers, and a heavy eaves cornice. The hipped roof dormers have slate shingle sides, and three windows on the front. The upper sash of the windows have a central diamond-shaped pane surrounded by four polygonal-shaped corner panes. The projecting, molded cornice is supported by modillion blocks over a brick dentil course. The facade has five bays of paired 2-over-2 windows. The central bay of the first floor, formerly the main entrance, has been filled in, and the main entrance is now on the west elevation. The effect of a series of string courses in the walls is created by recessing the brick by the depth of one brick at the window lintels and sills of the first and second floors. Recessed panels between the first and second floor windows and between the basement and first floor windows are an additional refinement. A plain, 1917 brick addition on the rear is given over primarily to an auditorium.

The houses along both sides of the Boston Post Road between the Town Hall, or school, and the church, and on the west side of Brookside Road across the street from the church, are modest frame structures, all with gable roofs. Perhaps the four oldest, and smallest, are 694, 701 and 728 Boston Post Road and 5 Brookside Road. Now altered, all originally were rectangular, 1-1/2-story three-bay clapboard houses on stone foundations with the roof ridge parallel with the street.

A second design type amongst this group of houses is the T-shaped plan of which three examples, originally identical, exist at 676, 682, and 688 Boston Post Road. These are 2-1/2-story clapboard houses on stone foundations with entrance in one of the angles of the T. Windows are 4-over-4 double-hung sash with the exception of those in the first-floor bay, and in the attic. The one-story, rectangular bay on the front of the stem of the T, which projects toward the street, has paired 2-over-2 windows. The attic gables, that are covered by wood shingles with convex-shaped corners, have four-pane windows, the upper pair shaped like gablets. A larger and more elaborate version of the same T-shaped plan is seen at 11 Brookside Road. In addition to the basic plan, the decorative detail of the rectangular, one-story bay with paired 2-over-2 windows is repeated there, with similar horizontal panels below the bay windows. Raised moldings forming a diamond pattern in the ends of the flanking porch roofs are also found in the row of three smaller houses, while in the larger house the shingled gable ends have attic windows of a central, large pane surrounded by a border of small lights.

A third design that is represented by more than one structure is shown by the pair of houses at 679 and 685 Boston Post Road. They are small, combination clapboard-and-shingle, 2-1/2-story houses with the roof ridge perpendicular to the street. The facade of the first has a door and a large 2-over-2 window at first floor with three 1-over-1 windows at the second floor, and a shingled second floor that flares over the clapboard first floor. The second is a three-bay clapboard house with the picturesque attributes of fish-scale shingles in the gables and cobblestone foundations.

Three older houses constitute a fourth design group. Two of them are located on Old Kings Highway North. The Bates-Scofield House (Historical Society of Darien), 45 Old Kings Highway North, dating from 1736, is a five-bay, 2-1/2-story, clapboard saltbox with central stone chimney and central doorway on stone foundations. The windows are 9-over-6. A two-story, gambrel-roofed ell to the rear was added after the house was moved to its present location in 1966.

The Joshua Morehouse House, 70 Old Kings Highway North, c.1730 is a 2-1/2-story, gable-roofed, central entrance house with small central brick chimney and clapboard siding. During the course of alterations about 1835 the house received a Greek Revival style portico, doorway, and eaves cornice. A porch with Doric columns on the north has a screened-in porch above, and there is a screened-in porch on the south.

The third house in this group of older structures, not on Old Kings Highway North, is the Sylvanus Weed, Jr., House, 25 Brookside Road, c.1770, another five-bay, 2-1/2-story, gable-roofed Colonial with central doorway and central chimney. The windows are 12-over-8, and the siding is wood shingles, painted white. This house also has a two-story addition, at the southwest corner.

Other structures, one of a kind, that fill out the balance of the Boston Post Road Historic District, are several 20th-century houses, including the church parsonage at 18 Brookside Road and the Y.W.C.A., at 49 Old Kings Highway North, and two vernacular late 19th century/early 20th century houses at 693 Boston Post Road, and 1 Brookside Road. 714 Boston Post Road, a Queen Anne house with a large concrete store front is considered, because of the insensitive addition, not to contribute to the historic character of the Boston Post Road Historic District.


The buildings in the Boston Post Road National Register Historic District illustrate architecturally the development of the community from the time of its settlement to the 20th century. Included in the Boston Post Road Historic District are good examples of the pre-Revolutionary War, Greek Revival, Italianate, Queen Anne, 19th century vernacular, Neo-classical Revival, Georgian Revival, and 20th century contemporary styles. The Boston Post Road Historic District is an architectural statement of the history of Darien that is well worth preserving.

History of Church and School

The movement for a separate Ecclesiastical Society in western Stamford in the 1730s was vigorously opposed by Stamford's First Ecclesiastical Society for several years, but in due course the insurgents prevailed, and the Middlesex Ecclesiastical Society was authorized in October 1737. Why this section of Stamford was called Middlesex is not known, and, similarly, why the name Darien was adopted when the separate town was incorporated in 1820 is not known.[1] The first meetinghouse, built on the present site in 1740, is shown by a Barber sketch (1835)[2] to have been a 2-1/2-story frame structure with its gable roof perpendicular to the street.[3] Its three-bay facade had a central doorway under an open belfry that was capped by a short steeple and a tall weathervane.

The Middlesex Society School was built on the triangular land immediately south of the church, and in due course the post office was established across the street, to the west of the church. In many New England communities, public buildings such as the church, school and post office often were located around a central, open space, but there is no indication that Darien ever had a village green such as is typically found elsewhere.

Establishment of the Ecclesiastical Society pre-dated the Boston Post Road, put through after 1800. Old Kings Highway North, is probably the oldest street in the Boston Post Road Historic District, and was long-known simply as County Road. Brookside Road, originally Gracious Street, is another old road; it adjoins and runs parallel with a brook named Goodwives River, earlier Pine Brook. Further name changes are indicated by an 1893 map[4] that shows Old Kings Highway North as the Old Boston Post Road, and the present Boston Post Road simply as Main Street.

In 1740 Dr. S. Moses Mather began a long term of service as pastor of the church that continued to 1806. At the time of the Revolutionary War he provided leadership for his congregation in support of the revolt, but there was no unanimity in the community as a substantial number of local citizens were Tories. Mather and four of his sons were abducted in 1779 by local Tories and held for a month before being released. In a more famous incident, on Sunday, July 22, 1781, forty local Tories took over the afternoon church service, tied up the males, led them out of the church two-by-two with Dr. Mather at their head, and also absconded with 40 horses. Twenty-five of the prisoners eventually reached the British Provost prison in New York City; 19 survived.[5] Thus, the Tory cause received strong support in the Middlesex parish up to the very end of the Revolutionary War.

In 1837 the society replaced its first meeting house with the present structure, which they modelled after the Old Wells Meeting House in nearby South Norwalk (demolished).[6] The architect and builder remain anonymous. A 600-pound bell was installed in 1841. In 1903, in line with the trend to merge ecclesiastical societies and congregations, use of the term Middlesex Ecclesiastical Society was discontinued, and the name First Congregational Church Society of Darien was adopted.

The term Middlesex had already been abandoned so far as the school was concerned in 1838, with a change of name to Darien School Society. In 1858 there is reference to a Centre School District. The 1832 school building was considered to be inadequate by 1878, and in that year was replaced. The 1832 structure was sold, and was moved to Railroad Avenue (now Tokeneke Road). The new school was built in 1878 on land that is now the parking lot behind the Town Hall. "It was a stately structure, with a belfry containing a bell,"[7] and in a contemporary picture is shown to have been in the Queen Anne style with bargeboards, and elaborate strut and a finial in the gable end facing the Post Road. The present structure was built in 1910 as a new Centre School,[8] and was converted to use as the Town Hall in 1949.[9]


Architectural significance of the Boston Post Road National Register Historic District does not derive from the excellence of the individual structures. Only the church and the school have pretensions of grandeur, and while competently designed, they are representative of common practice followed at their respective times of construction. The Greek Revival style church has excellent proportions and an impressive portico but the portico is without elaborate moldings and the tower is without a steeple. The Neoclassical Revival style school is also well proportioned, has perhaps outstanding roof treatment, and the brickwork of the facade is elaborate. But it was a fairly standard design for its time. Many such schools were built after the turn of the century, and many have been demolished.[10]

The architectural contribution of the church and school to the Boston Post Road Historic District is far outweighed by their function as anchors, east and west, for a group of structures that as a whole give insight into a historic way of life in Darien that is far different from its usual image as a residential community for New York City commuters. A great deal of Darien's 18th and 19th century history is tied up in the church and school and surrounding buildings. This effective sense of a former time and place now surrounded by metropolitan and commuter living is the great contribution of the district.

Unfortunately, little is known about the origin and purpose of the modest 19th century frame houses. The small, rectangular, three-bay houses probably go back to the 1830s, but there is little information on community conditions at that time. There is reference to a hat manufacturing shop near the corner of Brookside Road and the Boston Post Road, (where the gasoline station is now). The creek was used to soak the felts. As the next town east is Norwalk, long famous for hat manufacturing, it is easy to think that some of the activity may have spilled over to nearby Darien. Also, there is a local oral tradition that the small, three-bay house at 4 Brookside Road was a shoemaker's shop and that shoes were made in the basement of 25 Brookside Road. Such modest enterprises are conceptually consistent with the modest architecture.

More information is known about the four T-shaped houses between the church and the school. The large house, 11 Brookside Road was built by Joseph Hindley in the 1880s. In 1888 he acquired the land behind this house that fronts on the Boston Post Road, and built the three identical houses, that are a smaller version of his own, at 676, 682 and 688 Boston Post Road. He rented them for several years before selling them about 1900.

The three older houses provide an important connection with the 18th century, but again are primarily notable for their associations and for the fact that they have survived, rather than for their architectural integrity. The Bates-Scofield Homestead (the Historical Society), where the first business meetings of the Middlesex Ecclesiastical Society were held in 1739, is a highly competent restoration, but the house is not on its original site, and does have an extensive wing that was added in recent years. The Joshua Morehouse House, 70 Old Kings Highway North, and the Sylvanus Weed, Jr., House, 25 Brookside Road, have significant additions and alterations. Their importance lies in linking the Boston Post Road Historic District with the 18th century; they add substantially to the architectural historic record.


  1. Hughes, p.107. The Register and Manual, 1981, State of Connecticut, page 599, states that the town was named from the Isthmus of Darien. Hughes considers this possibility to be one of several.

  2. Reproduced in Darien Historic Sketches, p.7.

  3. In the 1920s plans were drawn for a structure somewhat similar in appearance to serve as a parish house (see The Church with a History, frontispiece) but were not executed. The architect was Hobart Upjohn, son of Richard M. Upjohn, who designed the Connecticut State Capitol.

  4. Atlas of the State of Connecticut, p.124.

  5. Hurd, p.268.

  6. The Church with a History, p.30.

  7. Corbins, p.45.

  8. The name was changed in 1921 to Royle School in honor of Edwin Milton Royle, a playwright and actor, who lived in Darien 1909-1920. See Corbins, p.61.

  9. In 1878 the land was purchased from the heirs of Eleanor Shay, (Darien Land Records, volume 8, page 891 and 8/894) who had lived at 701 Boston Post Road. For the 1910 building program see Town Meeting Minutes, v.4, p.130; for the 1917 program v. 5, p. 49.

  10. Schools of this description are standing, two in each community, in Torrington and Mystic, Connecticut.

  11. Case, p.8.


Atlas of the State of Connecticut, Boston: D. H. Kurd & Co., 1893. Henry J. Case and Simon W. Cooper, Town of Darien, Darien: Darien Community Association, 1935.

The Church with a History, Darien: First Congregational Church, nd (c. 1925).

J. Benjamin Corbins, Historical Account of Events in the Order of Time Which Have Taken Place Between 1641 and the Present, nd (1948).

Darien Historical Sketches, Darien: Darien Historical Society, 1970.

Arthur H. Hughes and Morse S. Alien, Connecticut Place Names, Hartford: Connecticut Historical Society, 1976.

D. Hamilton Kurd, comp., History of Fairfield County, Connecticut, Philadelphia: J.W. Lewis & Co., 1881.

Frances Landon and Nancy DiJoseph, Notes on research in the Darien Land Records, at the Historical Society of Darien.

David F. Ransom, consultant, and John Herzan, Connecticut Historical Commission, Boston Post Road Historic District, nomination document, 1980, National Park Service, National Register of Historic Places, Washington, D.C.

Street Names
Boston Post Road • Brookside Road • Old Kings Highway North • Route 1