Winthrop’s Main Street underwent modernization in the 20th century, as more of the town’s population shifted from rural farms to centralize in the main village area. Prior to the 1920s, peddlers served much of Winthrop with their deliveries, but increased transportation via car and trolley transformed the downtown area into a shopping center. Many of Main Street’s stores were remodeled, while new businesses, including some chain stores, sprung up along the street.

The caption reads, "Main Street, Winthrop, Me."

The Tichnor Brothers printing company published this type of postcard circa 1938.