[Chicago Sandy]

Hate to rain on anyone's parade, but there is no 1st Amdmt. right to busk without a permit. If the Constitution applies at all it is to protect the content of what you're singing as long as you are singing lawfully If there are public safety and noise ordinances, courts have held that performances and demonstrations which violate those ordinances--e.g, are noisy or obstruct traffic (including pedestrians)--can be prohibited.

I don't know about your part of MA, but I have acquaintances who busk in Boston, and a permit is necessary. Moreover, you can only have a small battery-powered amp if you don't play or sing unplugged (and for awhile they'd outlawed amps in the 'T tunnels). Here in Chicago, a friend of mine helped develop our busking license ordinance (before the ordinance, busking was considered disturbing the peace and led to many arrests, usually purely revenue-generating). The city realized that they could make more off a $10/yr. per artist permit ($30 when last I checked) than they could off fines that starving musicians couldn't pay (and it cost money to keep them in lockup). Back in the earliest days of our ordinance, I used to busk along with the musicians and show the cops our permits and a copy of the ordinance. We never did get busted but we always got requests.....