The district is located in the southern portion of Madison, west of the town center along the Boston Post Road (US Route 1). It is a linear district focusing on those buildings along the Boston Post Road between West Cemetery (Jannas Lane) and Ox Pasture Road (to the south of the Boston Post Road) and Mungertown Road (to its north). It includes most of the buildings with an address on Boston Post Road along this portion of the road (i.e., numbers between 248 and 420). It also includes properties that abut the Boston Post Road Street but have addresses on other streets: one property with a Fort Path address and two with Neck Road addresses. Four properties, 27 Fort Path (West Cemetery) and three on Boston Post Road (MBLU 36/46, MBLU 26/12, and Lowery Field), do not include buildings. The district includes 51 resources including properties without buildings.

The Old Elm Street Historic District is a predominantly residential neighborhood with a diverse collection of houses from the Colonial period through the modern era located along US Route 1 or the Boston Post Road. The buildings in the proposed district demonstrate changes in taste and style, but they are also indicative of how land use in Madison has changed over time. Beginning as an agricultural area, the proposed Old Elm Street Historic District transformed into a residential neighborhood during the nineteenth century. By the second quarter of the twentieth century, agriculture was barely practiced in the area; the farms had been subdivided and developed for more housing. The process of subdivision has remained a constant along the Boston Post Road, with new houses appearing throughout the twentieth century, spurred by the need for more housing and due to increased accessibility (via the Connecticut Turnpike) in the middle decades. The presence of the historic West Cemetery, Lowery Field, and the Madison Country Club’s golf course have helped to maintain open space within the district. The road itself also has had a changing role during this period: it began as a Native American path, provided access to the ecclesiastical and governmental center in Guilford prior to Madison acquiring its own meetinghouse (and ultimately becoming a separate town), and became a vital link for the transport of information along the coast via mail. Its importance as a transportation link grew with the addition of the streetcar and then the burgeoning popularity of automobiles, before being supplanted by the Connecticut Turnpike in the middle of the twentieth century. Throughout this time, it has remained a residential neighborhood, a rarity highlighted by its designation as a Connecticut State Scenic Road in 2008.

Old Elm Street’s historical significance lies, in part, in the fact that it has remained a residential neighborhood. The historic character of Route 1 through Connecticut has been lost in many places as the road has become lined with commercial establishments, strip malls, and roadside attractions. That has not been the case with the Old Elm Street district, where the road presents a clear picture of the additions and adaptations that have occurred to the buildings to allow the neighborhood to retain its residential character for more than 300 years.

Preserved along its streets are examples of structures and properties from the town’s agricultural past next to examples built for nineteenth-century craftsmen and near others that were constructed to house (or have been converted to house) commuters to nearby cities. Also preserved in the district is a physical reminder of the way in which cars have transformed the landscape. By preserving the buildings along Boston Post Road, the district protects a rare opportunity to travel along a relatively unchanged section of US Route 1. Traveling at relatively low speeds, one can see that car travel in the early twentieth century was an experience far different from current travel along a modern highway. Taken together, all of the elements in the district provide a physical reminder of the important role of history in shaping the town’s identity.