The Boston Post Road made Weston prosperous. Following an aboriginal trail connecting the Boston Basin to the Connecticut River valley, the Post Road eventually provided access to New York City. The first post rider service was inaugurated in 1673. The popularity of this route continued until the early nineteenth century when two turnpikes north and south of Weston diverted much of the traffic. The entire length of the Post Road in Weston is a National Register district. The Town Green is the commercial and institutional core, made less busy by a 1931 bypass. The principal document of colonial commerce on the Town Green is the clapboard gambrel-roofed Josiah Smith Tavern (1757, 1763 enlarged, 358 Boston Post Road), now town offices.
Much of the character of the current Town Green District derives from a village beautification effort inaugurated in 1913, the bicentennial of the town. Landscape architect Arthur Shurcliff established a new town center by draining a swamp and designating the sites for new public buildings around the green. Bigelow and Wadsworth designed the Weston Town House (1917, 2001 addition, Town House Road), a model of Colonial Revival red brick civic design with colonnaded portico and delicate cupola, and local architect Alexander Jenney added the brick gambrel-roofed Weston Fire Station (1913–1915 enlarged on east, west, and south, 1986–1988, 394 Boston Post Road). Jenney's firm, Fox, Jenney and Gale, had previously designed the Weston Town Library (1898–1899, 354 Boston Post Road), a domestically scaled brick Tudor composition next to the Josiah Smith Tavern. Diagonally across from the library, Peabody and Stearns erected the Unitarian First Parish Church (1883–1888, Boston Post Road and Church Street), a Gothic English parish church design constructed of boulders with a brick interior, windows by Tiffany and Connick studios,