Winter Island at the time of English settlement in the early 17th century was an island separated from the mainland, held as common land by the Proprietors and used as a fortification and for fishing activities. In 1643 Fort William was begun on the island.
18th century
Circa 1702, during Queen Anne's War, Fort William was renamed Fort Anne, and was rebuilt around 1706 under the direction of the Royal Engineers, who were earlier sent by King William III to fortify the colonies. It is unclear how much was accomplished, as a debate on whether the town or the province should fund the rebuilding lasted past 1711, when the war ended for the American colonies. In 1735 the Massachusetts General Court provided 600 pounds to rebuild the fort to hold 15 guns. It was rebuilt again by the town and known as Fort Number Two in Patriot hands during the American Revolution. In 1794, the City of Salem ceded the fort to the federal government and a new fort was constructed in its place, part of the first system of U.S. fortifications. The 1794 U.S. Army report on fortifications called for the fort to have eight artillery pieces, a blockhouse and a magazine. The fort's garrison was proposed to consist of one officer and 22 enlisted men. Major repairs to the fort were conducted in 1796 and a restoration in 1799. Later in 1799 it was renamed Fort Pickering in honor of Timothy Pickering, then Secretary of State of the U.S.
19th century
The fort was rebuilt in 1800 and 1808 to mount six guns. In a report on the conditions of fortifications of the United States submitted to Congress by President Jefferson on January 6, 1809, the following is stated regarding Fort Pickering - "The fort and block house,... with a magazine under it, have been repaired and a new barrack erected." Another report in December 1811 stated the fort was "an enclosed work of brick and sods, mounting six heavy guns, covered by a block house". Regular Army commanders of the fort from 1800 to 1812 included Capt. Alexander D. Pope 1800–1802, a detachment of Capt. Nehemiah Freeman's company 1802–1803, no federal garrison 1804–1808, and Capt. Stephen Ranney 1809–1812. Massachusetts militia camps on Winter Island in the 1850s and 1860s included Camp Sutton, Camp Edmunds, Camp Banks, and Camp Gardner. Camp Sutton existed in 1853 and 1855. The camp was named for general William Sutton and was occupied by the 2nd Division. Camp Edmunds existed in 1856. The camp was named for Major General B.F. Edmunds and was occupied by the 4th Brigade. Camp Banks existed in 1858. The camp was named for Major General Nathaniel P. Banks and was occupied by the 2nd Division. The fort received another military restoration in the War of 1812, during the period of the second system of U.S. fortifications. In 1820 it had a capacity of 11 guns. During the 19th century, the island was used primarily for fortification and in 1864 the City of Salem again ceded the island to the federal government in support of the Civil War efforts. Although the capacity remained at 11 guns, the area of the fort was increased, with earthwork parapets built outside the stone fort and gun embrasures added for improved protection. The magazine was also increased in size. An armament report by Major Charles E. Blunt dated January 31, 1865 shows the fort had six 24-pounder smoothbore guns, three 32-pounder rifles, and two 24-pounder rifles. It was also called Salem Barracks in that war. From May 1864 to June 1865 Fort Pickering was garrisoned successively by the 3rd and 17th Unattached Companies Massachusetts Volunteer Militia.
20th century
In 1935 most of the land on Winter Island became the newly established Coast Guard Air Station Salem. The air station had a hangar and ramp for seaplanes. Aircraft from the station conducted anti-submarine patrols during World War II and search and rescue missions until it was closed in 1971. The site was added to the National Register of Historic Places in 1973. In 1994, the National Register designated the entire collection of cultural resources at Winter Island and Fort Pickering as the Winter Island Historic District and Archaeological District. Portions of the Civil War fort remain.
