[2] The square was named in honor of Admiral George Dewey after his decisive 1898 victory in the Battle of Manila Bay.

Before the Central Artery construction of the 1950s, it was simply an intersection with traffic islands and rail infrastructure, surrounded by buildings with no open space.

Around this time, the Boston Elevated Railway reorganized its streetcar tracks into a grand union at the intersection of Summer and Atlantic.

For some time, a temporary intercity bus depot for providers such as Peter Pan, Trailways and others was located just north of Dewey Square over the Central Artery.

From September 30 to December 10, 2011, Dewey Square was the site of the Occupy Boston tent city.