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Once known worldwide as "Rosetown," Cromwell has enjoyed multiple identities in its nearly 370-year existence. Initially called Upper Houses, the village was a tiny religious and agricultural outpost of the larger Middletown colonial settlement on the Connecticut River. Gradually, substantial maritime activities developed to define the community. However, by the mid-19th century, Cromwell had become an independent rural town with small farms and businesses, its river port no longer of consequence. Later, the famed greenhouses and floral industry provided international recognition. Small manufacturers and quarries also contributed to the economy. By the late 20th century, the village had become a suburban community, its cohesion impacted by the construction of major highways as well as significant commercial and residential development. At each incarnation, the town has pushed out toward its defining geographic boundaries, and the conflict between the old and the new has created changing patterns of social, economic, and political organization.

Stafford, nestled in the hills of Northeastern Connecticut, was settled in 1719. Originally an agrarian community, the town has a diverse history. The discovery of iron ore led to a thriving iron industry that produced various items, including cannons and shot for the Continental Army during the American Revolution. The mineral springs, long known to the Native Americans, became a destination location, attracting visitors such as John Adams, future president of the United States. Stafford hosted one of the earliest agricultural fairs in the state, which ran until 1969. The biggest influence on the town was the introduction of the textile industry in the early 19th century. As immigrants of many ethnicities came to town to work, Stafford experienced unprecedented growth and the population diversified. Stafford's mills became major contributors to the country's textile industry, particularly wool manufacturing.