The North American Vexillological Association (NAVA) conducted a survey in 2001 that ranked Maine's current flag as one of the worst in design.

Originally, the 1901 Maine flag consisted of a green pine tree, a Indigenous-derived symbol of New England and freedom, in the center, with a blue "North Star", all on a buff-colored background.

It features symbols from the current flag and the older one, with a white field and green pine tree.

About a dozen or so portions of these flags still exist, including one at the Maine Historical Society still mounted on its original pole.

The last known instance of a Maine militia unit using this flag was in 1861 at the First Battle of Bull Run, which was recorded as being captured by Confederate forces.

[9] Secretary of State Matt Dunlap submitted three designs for public comment: one of his own design, one using the Maine Bicentennial Committee logo, and a third based on Van West's flag, but replacing the white star with the red/gold/white Dirigo Star from the state flag.

[10] After the third design won the contest, Van West offered Dunlap a further revision replacing the multicolored Dirigo Star with a monochromatic white version.

[15][16] On August 5, 2024, the winner of the flag redesign contest was announced, with honors going to Adam Lemire of Gardiner, Maine.

His design, chosen out of more than 400 entries, features a pine tree modeled after one he saw in Viles Arboretum in Augusta, Maine.