The track of Bob by late August 18 and early August 19 was similar to that of Hurricane Carol in 1954, another major hurricane that impacted New England. Significantly cooler sea surface temperatures in the path of the hurricane resulted in weakening, leading to the eye becoming cloud-filled. Later on August 19, the western portion of the eyewall brushed the eastern tip of Long Island. Around 1800 UTC, the center of Bob made landfall near Newport, Rhode Island, with winds of 100 mph (155 km/h), making it a Category 2 hurricane. The storm quickly weakened as it tracked through Rhode Island and Massachusetts before entering the Gulf of Maine. Around 0130 UTC on August 20, the now weakened Tropical Storm Bob made another landfall near Rockland, Maine.