John E. Cochran opened the first insurance agency in Windham in 1924. Eventually his son became a partner in the business, and the name was changed to "John E. Cochran & Son Agency." They remained the only insurance business in Windham until George H. Butterfield, Jr. opened an insurance agency in 1951. The Cochrans operated their agency until 1962 when they sold the operation; the business did not continue to operate in Windham. For one year Butterfield was left the only insurance agent in town, until Eleanor Zins opened her agency in 1963; Zins closed her business after only one year. By the early 1970s Butterfield had sold his insurance business, and for the past four decades various insurance agents have operated in Windham.