There are old photos of schooners half buried in the thick harbor ice as groups work right on the ice. That sheet of ice as we know, goes up and down 10', twice a day. Any seas from a southerly wind will knock it to pieces in short order. I doubt we'll see those days of that much ice in Rockport, again.
There are two sailboats spending the winter in the outer harbor. That seems foolish to me. Maybe they'll survive the winter gales but it's nearly impossible to get to them through the inner ice, and there's no docks to bring them into if they need attention. Leaving a boat in like that is a financial decision I'm afraid, very risky.