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Keep in mind, it's your chief, who determines the restrictions he wants followed in your (his) town. What happens two towns over, is anybody's guess. Can you carry there? Who knows? Can you tell the cop, "my chief says it's OK to carry, cuz I'm on my way to the range?" Maybe you'll be fine, maybe you won't.
I don't think this can ever be answered definitively without a court case.
You really need a signed letter defining HIS meaning of your restriction from your LTC issuing chief on letterhead WITH YOU to avoid the doubt that can lead to headaches.
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To add to this thread:
Middleboro currently takes applications and renewals on a FIRST COME FIRST SERVE, 10 SPOT LIST.
You must be one of the first ten people in line, every thursday (barring Holidays) or you're SOL until next week and you must try again.
Applications are processed ONLY through that system and the PD is not responsive to mail-ins.
Very common PD response but also a direct violation of MGL as passed in August 2014. The arrogance of tin-pot dictators is legion however.