Windham is a town of many contrasts—from the colonial charm of Windham Center, where the town was founded, to the Victorian splendor of Willimantic. Windham is a community proud of its past as shown by the careful restoration of Willimantic, but also looking forward to the future as shown by its approach to land use and zoning. Windham offers a rural charm in much of the town, yet has all the services of a city in Willimantic.

First settled in about 1686 by descendants of Norwich men who received the land as grants from Uncas’ son Joshua, the Town, named from Windham in Sussex County, was incorporated in 1692. The area in the vicinity of Willimantic was settled to take advantage of the river’s water power for saw and grist mills. In later years, the town was dominated by the thread and textile industry. The town was known worldwide as one of the finest manufacturers of thread outside of England and was aptly named the Thread City. It was chartered as a borough in 1833, a city in 1893 and in 1983 it was consolidated as part of the Town of Windham.

The population of Windham increased from 3,428 in the first U.S. Census of 1790 to 5,412 by 1870. The next decade recorded the greatest growth in the town's history and by 1900 the town had nearly doubled in size totaling 10,137 residents. According to the 1970 U.S. Census figures the population of Windham was 19,626 with a 1960 population of 16,973. The 1980 U.S. Census placed Windham’s population at 21,062. (the Census count does not include approximately 1,250 in group quarters. Group quarters include dormitories, institutions, and nursing homes). The 2000 Census shows a current population of 22,857 which is only a 818 increase over the 1990 Census.