Hurricane Hugo was a powerful Category 5 hurricane that struck Guadeloupe , Montserrat , Puerto Rico , St. Croix , South Carolina and North Carolina in September of the 1989 Atlantic hurricane season , killing 82 people and leaving 100,000 homeless . Hurricane Hugo was a destructive Category 5 hurricane that struck Guadeloupe , Montserrat , St. Croix , Puerto Rico , Antigua and South Carolina in September of the 1989 Atlantic hurricane season .