Winter Island has a history that predates Salem.

When Captain John Smith navigated the coast and drew maps in 1614, the island was home to the Naumkeag who used it as fishing grounds.

Roger Conant and his group of Planters, in founding Naumkeag in 1626, immediately recognized Winter Island’s importance. It was named Winter Island after its sheltered Winter Harbor, which offered a safe harbor for their all important fishing boats that needed protection during  winter storms. Winter Island immediately become home to the fledgling fishing industry. It was here on the remains of abandoned native settlements that early settlers dried the fish caught and built their homes as well as along Salem Neck.

As the fleet and population grew, Winter Island and its environs became a
center of activity for Salem. It was here that the town first licensed in 1637 a public house to meet the needs of the residents, fishermen, and visitors. This area was the working area of Salem for many years. With the growth of trade, Winter island continued to hold an important role in providing fish for trade. During the 1600s, there were some 10 wharves extending into Cat Cove. By 1698, streets and ways were laid out across the island many following prehistoric Native American paths. The main thoroughfare was called Fish Street. In 1714 the commoners voted that Winter Island be reserved for fishing and some pasturage.  As demand grew, shipping spread along the coast of Salem.

Due to its geography, Winter Island and the adjacent Salem Neck were obvious choices for forts to protect the fleet and town from hostile nations. Winter Island became home to forts, where the cannons could ward off any attacks from the sea. In 1643, the first fort was established. In 1699 it was named Fort William, then changed in 1704 to Fort Ann. Salem, thanks to these forts, was the only New England port not captured during the War for Independence. The Fort was renamed in 1799 for Salem's Timothy Pickering, Secretary of State in George Washington’s first administration.

Winter Island, in addition to being a site for forts, was also home for one of Derby’s early commercial wharves and a vibrant ship building industry. Nearby to Derby’s Wharf was a powder house for the storage of gun powder for arming privateers.  It was here on the southern side of the island that in 1799 the largest ship ever built in Salem was launched. The 800-ton Frigate U.S.S. Essex, paid for by the merchants and people of Salem and Essex County, was given to the U.S. Navy. The ship saw intense action, capturing more than a dozen ships during the War of 1812, before it was seized in a sea battle off of Chile.

When we think about executions in Salem our first thought usually goes to Gallows Hill and the Witch Hysteria executions. There is, however, another place of execution in Salem that was the official site of four executions between 1772 and 1821 — Winter Island. After 1821 all executions were moved to the Salem Jail on St. Peter Street. These executions usually took place in the courtyard.

The public place chosen for public executions was the highest hill on Winter
Island known as Execution Hill. This hill had the advantage of being a rocky one with much open space around it to accommodate the tens of thousands who would gather to witness the event.

In 1792 the first of four executions was performed on Execution Hill which corresponds today to the area of the abandoned Coast Guard Administration building. Bryan Sheehan, 39 years old, who was convicted of rape, was hanged on Jan 16, 1772. According to news reports of the day some 12,000 people attended the execution. At the time, Salem’s population was less than 8,000. On Dec. 21, 1786, Isaac Coombs, a 39-year-old Native American was executed for the murder of his wife.

On Jan 14, 1796, Henry Blackburn, convicted of robbery and murder, was executed. On May 10, 1821, 16-year-old Stephen Clark was executed for arson.

This last execution was very notable in that it generated much talk as well as signed petitions to reconsider the use of the death penalty for what was considered Capital Crimes. This boy, who had a troubled youth in Newburyport, supposedly fell in with problematic companions and set fire to a stable in Newburyport that resulted in several buildings being destroyed and people barely escaping with their lives. His age and the set punishment generated a lot of controversy as well as one attempt to break him out of jail. Some 20,000 people attended this last execution. From the numbers it is obvious that literally thousands came from across the region to see this.  

These executions were major events that thousands attended. On execution day, the condemned was taken from jail to church in an open cart where he sat on his future coffin. At church the minister would lecture on his sin and approaching fate. After the service he was returned to jail for his last meal, then once again sitting on his coffin, brought from the jail to Winter island, where people would have been waiting for the condemned’s arrival. Upon arrival at the gallows, the charges were read, along with any statements from the condemned. If the prisoner was too overcome, the statements, usually an admission of guilt and a charge to others to avoid this fate, were read by one of the ministers who accompanied the prisoner. The condemned was then made to stand on his coffin while the noose was put around his neck. Once secured, the cart was moved and the prisoner was hanged.

As Salem’s commercial interests shifted to other parts of the city, Winter Island and its forts became paramount. Whenever a war occurred, the forts were refurbished and utilized for defense of the coast. Modernization of the Revolutionary Fort Pickering occurred during the War of 1812. The fort was expanded and brought up to standards during the Civil War, then again modernized for World Wars I and II.

In the late 1870s, a lighthouse was built and a small residential area developed at the northern entrance to the island. The Plummer Home for Boys was built just south of Winter Island Road during this time.  In 1933, some 20 of the island’s 38 acres were given over to the Federal government for a coastal defense installation and later a Coast Guard Air & Sea Search Rescue Station. The airplane hanger and Brick Revival barracks buildings remain in various states of disrepair. The Coast Guard maintained a presence here until 1969, when it abandoned the property.

Winter Island was reclaimed by the city in 1972. It was then designated a marine park. This area today also houses a RV park that is very popular throughout the summer months. It also hosts many public and private events that draw visitors from across the region and country. City residents may recall this area as an excellent vantage point for watching the 4th of July fireworks for Salem and surrounding towns. The increased activities at Derby Wharf as well as the fees for residents to enter Winter Island has lessened the popularity of this viewing spot.

In 1988 during an Archaeological Survey for the City of Salem, the noted archaeologist, Stephen Mrozowski wrote at length about the significance of Winter island as a unique site, reflecting its prehistoric use, its development as a fishing and shipbuilding center, its strategically important location and its continued ongoing use with little heavy development.

He concluded his assessment with a strong admonition that, “This concentration of cultural resources combined with what appears to be relatively good integrity makes Winter Island an important site. No further construction work should be carried out on the island until an intensive archaeological survey has been completed.” The Massachusetts Historical Commission concluded that this site is eligible for inclusion in the National Register.

As the City continues to eye this important historical area as the possible location of a wind turbine, it is hoped that Dr. Mrozowski’s words will be heeded in order to preserve Salem’s rich heritage that rests here. This known and unknown history of Salem and Winter Island should not be lost or made inaccessible.