Maybe, but it would probably be the last state in New England to do so. It's younger, more urban and more diverse than Vermont, New Hampshire or Maine. If Republicans start to make inroads with those groups, the state could become more competitive down the road.
It really is one of the great anomalies of American politics that Republicans have held the governorship for 22 of the last 30 years while Democrats have legislative supermajorities and a near lock on the entire congressional delegation. Even he's a "RINO", maybe the MAGOP should take some hints from Charlie rather than sucking up to the orange idiot.
Yes, I could hypothetically see a future election where Massachusetts is the only New England state to vote Democrat in an election, due to Boston. Ironically that also happened in the 20th century, but with entirely different coalitions.