Main Street has always been the shopping center of Winthrop. With the adoption of the automobile the focus changed from essential general goods for the home and farm to a market that caters more toward inessential and luxury items.

The Tichnor Brothers printing company published this type of postcard circa 1938 as part of their Maine series. These, and other postcards, by the Tichnor Brothers Company are officially known as the Tichnor Gloss Series because the photographs were notoriously retouched on such a level that does not allow the postcards to be classified as photographs or paintings. The caption reads, "Main Street, Winthrop, Maine."