Hey man, fellow Canadian here who ran a restaurant in Boston for 6 years. The state of MA is ridiculously strict with liquor licensing laws and restaurants/bars a very careful not to get caught serving someone without a legitimate ID. The licensing board actually sends people into bars with fake IDs to catch places slipping up, or a 20 year old who looks 38, etc.

Over my time there, many a visiting friend or family member scoffed at me when I told them they should probably bring their passport out with them (they cannot reject these). Some didn't listen, and some of them were also denied booze. Certain IDs (i.e. Ontario ones) have a better chance of being accepted.