The treacherous waters of the Vineyard Sound and Buzzards Bay were tricky for novices to navigate. Early on in the island's history, island men began to make a large part of their living piloting boats past the dangerous reefs and towards the ports of New Bedford,
Providence, and Boston. Men stood atop Lookout Hill with spyglasses in hand, scanning the horizon for incoming whaling ships headed for New Bedford. When a ship appeared, the men would scramble down to the shore to their boats in a race to be the first to offer services as a pilot. In 1903, Cuttyhunk pilots guided as many as eleven ships a day to New Bedford harbor. The reefs were indeed dangerous. In 1847, the Massachusetts Humane Society established life-saving stations throughout the Elizabeth Islands, supplied with items needed by islanders to assist boats in trouble. The
lighthouse was decommissioned and torn down in 1947, replaced by a skeleton tower. The keeper's house was also destroyed. The tower that replaced the old light house is no longer functional. The only surviving structure from the lighthouse station is a stone oil house, and its door and roof are missing.
Notable shipwrecks • February 24, 1893 – The
brig Aquatic was wrecked off Sow and Pigs reef on the West End of Cuttyhunk. In that disaster, five Cuttyhunk lifesavers were killed at sea while trying to save the ship's passengers and crew. • November 27, 1898 – The passenger and freight steamer
Fairfax was wrecked off Sow and Pigs reef in the midst of the infamous
Portland Gale, during which it is estimated over 150 ships and 400 lives were lost. Despite the intensity of the storm, all passengers (6) and crew landed safely. • August 26, 1924 – The whaleship
Wanderer, the last such ship to leave New Bedford. She put to sea on August 25, 1924 and anchored near Cuttyhunk to await the completion of her crew. The next morning, the seas rose and the
Wanderer dragged her anchors, drifting toward Sow and Pigs. As the anchor chains snapped, the crew knew the ship was lost and abandoned it in two whaleboats. Cuttyhunk lifesavers set to sea to help the men make it to shore, but by the time they reached the area, the two boats had disappeared. One boat made it to Cuttyhunk, and the other to the Vineyard Sound lightship. Years later, the grinding stone from the Wanderer, which had been found prior, year unknown, was found propping up the old stairs that lead to the Cuttyhunk Corner Store. Once discovered under the steps it was set into the new floor of the gift shop, and can be seen front and center as one enters the gift shop. There is a clear engraving on the circular stone that reads Wanderer. • In August 1992, the
Cunard Lines ocean liner,
Queen Elizabeth 2 badly damaged her hull by running aground on a previously uncharted
shoal about south southwest of Cuttyhunk. The ship suffered $13.2 million in damage, and the company lost $50 million when the ship was out of commission. ==Population and culture==