every model but one had it turning to the west, 5 days before, and that didn't change. It was only a question of precisely where it would make landfall. The forecasters also called right the huge size (area) of the storm, and that it was a major factor in it's effects. (It was only cat 1 but it was compared to the hurricane of 1938 which was a cat 5, and would have been a lot more destructive).

I think his first mistake was heading OUT rather than in. His vessel was no aircraft carrier -- he didn't have the size or speed to outrun that storm or ride it out, and he should have known it. You don't screw around with hurricanes and there were plenty of options to seek safer harbors if he thought he was too exposed in New London. He could have gone further upriver, or to New Bedford, or Boston's bays to name a few options. There are commercial wharfs in Bridgeport and New Haven. Maybe he would have blown ashore or damaged the hull but he'd have less risk to crew and if he had to anchor there are harbors that have sandy beaches surrounding them; and salvage is a better option than sinking offshore.