• Whales Park - The tour kicks off in the heart of Boothbay Harbor at the town pier, offering stunning views of schooners, lobster boats, super yachts, and the bustling east side waterfront. This town has a rich maritime history, being home to sailors, sea captains, fishermen, shipbuilders, and even pirates!
• 10 Wharf St - What links Queen Elizabeth I, a ring, and Outer Heron Island? Could it be a claim on a $1 billion English estate?
• Boothbay Harbor Footbridge - Take a leisurely walk across America’s longest wooden footbridge, where you can enjoy breathtaking harbor views, including Maine’s oldest lighthouse on Burnt Island, with its storied past of keepers—some of whom never left the island.
• Opera House at Boothbay Harbor - Initially constructed as a lodge for the secret society of the Knights of Pythias, the Opera House was rescued from demolition by two famous rock stars. It has since become a world-renowned music venue and is reputed to be the most haunted building in Maine.
• Boothbay Harbor Memorial Library - A mysterious figure dressed entirely in black checked into the Hotel Fullerton and ventured out to see the ocean surf. Her identity and untimely demise remain unsolved mysteries nearly a century later.
• Oak Street - Local Wawenock leader Samoset was the first Indigenous person to make contact with Europeans, setting an example for us today.
• Boothbay Harbor Shipyard - Explore the Boothbay Harbor Shipyard Museum to discover more about this historic shipyard, where tall-masted ships have been constructed for nearly 200 years.
• Whales Park - The tour concludes where it began, with tales of classic seafarer superstitions and sightings of mysterious creatures by hundreds of credible witnesses along the Maine and Massachusetts coastline, known as The Great New England Sea Serpent.

• Walking map of Boothbay Harbor
• 10% off another Mysterious Harbor Tours e-bike or walking tour
• Mysteries to unravel and legends to trip on
• Snacks

• Gratuities

This tour through Boothbay Harbor’s snickleways offers a delightful blend of the town’s hidden history, local legends, and unsolved mysteries that will keep you pondering long after the tour concludes. An engaging local guide provides an overview of the area and shares all the insider details on the harbor’s most enigmatic unsolved death, Boothbay Harbor’s own sea serpent, and legendary treasure stories linked to many of the harbor’s islands. The tour includes a visit to the Boothbay Harbor Shipyard Museum, where tall-masted ships have been constructed for nearly 200 years.

• Our walking tour includes some steep inclines and uneven surfaces, including sidewalks, grass, and wooden walkways. Your guide can assist those who need help with inclines and uneven surfaces. We can also accommodate wheelchairs on a custom tour. Please contact us to discuss this option.

For a full refund, cancel at least 24 hours before the scheduled departure time.