This design is part of my 2009 flag proposal series (the flag designs from my old site with the most hits and ratings).
The current design
The current flag of Massachusetts is a typical American-style seal-on-a-bedsheet design, and as a result it is convoluted, unmemorable and uninspiring. In 2020, the flag came under intense scrutiny because the design seems to imply colonial violence: There is a sword hanging above a Native American figure, the beginning of the motto translates to “by the sword we seek peace” and the artistic rendering was directly based on figures and artifacts involved with killings of Native Americans. There is ongoing pressure with many groups and towns endorsing a redesign of the flag. As of 2021, the state senate and governor have officially decided to redesign the state seal and flag. Therefore, here is my proposal.
My proposal
First off, this design is simple enough to be remembered by a child, yet distinctive enough to be identified at a distance.
This design’s central feature is the pine tree, a symbol of the New England region, shipbuilding, peace and brotherhood. This symbol has been in use for hundreds of years by indigenous people (featured on the Hiawatha Belt), English colonists (featured on coinage) and independent Americans (featured on flags and coinage). The pine tree on a white field is directly inspired by the naval/maritime flag of Massachusetts, the flag of New England, the Bunker Hill Flag and George Washington’s 1775 Pine Tree Flag, all commemorating Massachusetts’ key role in the American Revolution. The six stars represents how Massachusetts was the sixth state to join the union. It does this by echoing the American national flag, where each star represents a state.
Green represents agriculture, forests and the land. White represents peace, the coastline and snow. Blue represents the sea, maritime history, the official nickname “The Bay State” and the Blue Hills, after which the state is indirectly named. The colours blue and white have been retained from the current flag, so all of their current symbolism can be carried over as well.
Vector files available on request.
View and share this concept on other sites:
Brian Cham's personal website 
Obviously the existing flag is terrible. Yours is a great replacement. The six stars harken back to appropriate history and the pine tree, which covers most of the west of the state (the parts not covered by Boston) is an appropriate symbol for, as you say, all of New England.