Winter Island, now connected to the mainland in Salem, has had a colorful history. It was the site of eighteenth century Fort Pickering, much of which still survives.
Winter Island Light, also known as Fort Pickering Light, was built adjacent to the site of the former Fort Pickering in Winter Island Park, in 1871 – the same year as Derby Wharf Light in Salem Harbor and Hospital Point Light in nearby Beverly. For many years before, Baker’s Island’s twin lights had served as the only guides to the harbor. With the addition of the new lights, mariners would line up Fort Pickering and Derby Wharf Lights after passing Baker’s Island on their way into Salem Harbor.
The lighthouse, built of iron lined with brick, exhibited a flashing white light 28 feet above sea level. The lighthouse, originally painted red, was built slightly offshore. A walkway connected it to the shore. A Coast Guard airplane hangar was erected on Winter Island in 1934. The Coast Guardsmen lived temporarily in the lighthouse keeper’s house until new quarters could be built. The lighthouse keeper’s house later became the officers’ club for the Coast Guard’s Air Station Salem on Winter Island. In 1944, Air Station Salem was officially designated the first Air-Sea Rescue station on the eastern seaboard. The Coast Guard left Winter Island in 1969, and at the same time the lighthouse was replaced by an offshore buoy. With no one watching out for it the old tower soon fell into disrepair. A group of concerned citizens and businesses formed the Fort Pickering Light Association in the early 1980s. The lighthouse was refurbished and the foundation was repaired, and Fort Pickering Light was relighted in 1983 as a private aid to navigation. The lighthouse received a facelift in 1999, thanks to a community development block grant. Today, The Friends of Winter Island (FOWI) work to promote and guide the preservation and restoration of endangered historic resources on Winter Island.