Fort Pickering and Winter Island: Marching around Salem's History

Salem's Winter Island has weathered witch trial hysteria, wartime invasion scares, and centuries of fishing fleets, yet most visitors never venture past the city's famous downtown. On this walking tour, you'll trace four centuries of coastal defense at Fort Pickering, from colonial earthworks to Civil War ramparts. You'll also hear how a Coast Guard air base once hunted German submarines from these same shores.

The tour starts at Fort Avenue on Winter Island Road, beside the Cat Cove laboratory, and follows the causeway onto Winter Island itself, once cut off from the mainland at high tide. You'll pass the site of Smith Pool, once the largest saltwater swimming pool in the country, and walk into Fort Pickering's ruins, where moats and parapets still trace the fort's Civil War footprint.

Along the way, you'll learn how Salem's privateers used these defenses to fend off British attacks during the Revolution, and how depth charges were once stored in concrete “igloos” during World War Two. You'll pass Fort Pickering Light, built in 1871, and stand on Execution Hill, where public hangings drew crowds of thousands in the 1700s and 1800s. The tour ends at a pier overlooking Salem Harbor, where ferries and schooners still come and go today.

On this 60-minute tour, you'll have a chance to:

• See the concrete “igloos” once used to store World War Two depth charges, now available to rent overnight
• Look out toward Baker's Island Light and Derby Wharf Light, both visible from Winter Island's shoreline
• Hear the story of a 1952 photograph taken here, considered the first daylight UFO photo ever recorded
• Stand where the USS Essex, a 36-gun frigate later celebrated in the Marines' Hymn, was built in 1799
• Walk along Waikiki Beach, with views across Salem Sound toward Beverly and Manchester-by-the-Sea
• Spot the remains of the Coast Guard barracks and hangar from Salem's former seaplane base

By the time you reach the pier, you'll understand why this unassuming stretch of coastline shaped so much of Salem's military and maritime history.