Transitory travel: This includes people who are passing through Massachusetts and permits travelers to drive through the State or to connect to their airplane, bus or train, or to stop at a highway rest stop, but this exception extends only so long as is reasonably required for the traveler to complete their transit, make any necessary airplane, bus, or train connection, or make use of travel services such as at a highway rest stop.
Not really, although they have been raising the quarantine levels lately.
You'll be fine, keep traveling
As of August 1st you are not allowed to travel through Massachusetts unless you register with the government to let them know that that's what you're doing
None I'm aware of , but it's best to call and ask
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