On August 19, 1991 Hurricane Bob lashed the Vineyard. It was the earliest hurricane in New England history and the second most expensive, after Hurricane Hugo two years earlier.

By mid-afternoon the next day, the sun was out and crowds of people were assessing the damage. Edgartown Harbor lay in shambles, with 84 vessels beached, sunk or capsized. Ponds were torn open to the sea along the south shore, and roads from Chappaquiddick to Gay Head were littered with branches and wires. A few roofs were missing, and two feet of water lapped at the outside of the A&P in Vineyard Haven. But overall, the Island breathed a sigh of relief.