Incorporated in 1714, Littleton began as a typical New England farming town. While it enjoyed modest growth through the early years, it was not until after World War II that the population began its steady climb. Two major highways, Route 2 in the 1950s and Interstate 495 in the 1960s, cut through the town, and Littleton became an attractive bedroom community with convenient access to the expanding technological industry of Massachusetts. The population rose from 1,447 in 1930 to approximately 6,300 in 1970, and industry began to overtake the dairy farms and apple orchards. Still, the impression of a rural setting, the open space, and an intangible quality of life contribute to the small-town character for which Littleton is celebrated.

Through vintage photographs, many never before published, Littleton connects the current generations with the town's past. Vintage photographs of homes that have changed in appearance or have been destroyed for expansion recall a time of farmhouses and open fields. The book also follows the growth of Littleton, including the emergence of the Conant-Houghton Company and the depot area, as well as the Long Lake and Lake Warren resorts.