Oakland’s Main Street runs from Church Street to the lower Main Street at an intersection near the Messalonskee Stream and has been one the main commercial streets in the town throughout its history. In the 20th century, Oakland’s Main Street was the site of the central Depot Square and included retail stores and other small businesses (many located on the Bank Block), offices, public buildings, banks, and hotels. As shown in this postcard, outside of the main business district, Main Street includes tree-lined blocks with residences.

The caption reads, "Lower Main Street, Oakland, Me."

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