Much of Keene’s present charm is linked to its transportation past. Historically, many of the streets in the community were designed in radial and grid patterns that linked Central Square to the outlying community. Keene’s present-day street layout consists of many circuitous streets and cul-de-sacs. In contrast to the predominantly grid-style street network of the past, which diffused traffic throughout Keene, the current network channels traffic from various neighborhood streets and concentrates it onto collector streets and arterials.

The role of the turnpike and the railroad is also evident in the layout of Keene and the architectural styles of the community’s buildings. The Third New Hampshire Turnpike, which operated between Boston and Bellows Falls, Vermont, was one of the region’s most important transportation systems at the time. Incorporated in Keene in 1799, this turnpike later became the route of the Cheshire Railroad, which connected Keene with Boston in 1848.

By the end of the 19th century, Keene was served by four railroads: the Cheshire Branch, the Ashuelot Railroad, the Manchester and Keene Railroad, and the Connecticut River Railroad. These railroads have played a pivotal role in Keene’s history. Though all the rail lines and many of the former railroad buildings have been removed or converted to other uses, the rail beds and most of the stone bridges that supported this infrastructure still remain. Today, these resources provide Keene and the Southwest Region with important trail corridors, connections and linkages to surrounding towns and states. Public transportation is still an issue within the community, however, with no convenient means to travel to or from Keene via bus or train.