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 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 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. The first meeting house, built on the present site in 1740, is shown by a Barber sketch (1835)- to have been a 2-story frame structure with its gable roof perpendicular to the street. 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 (see map), 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.

The 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 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 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. 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 modeled after the old Wells Meeting House in nearby South Norwalk (demolished). 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, the 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 a 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," and in a contemporary picture is shown to have been in the Queen Anne style with bargeboards, an 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 and was converted to use as the Town Hall in 1949.