Mysterious Lore and More Walking History Tour of Boothbay Harbor

This walk through Boothbay Harbor's snickleways is a wonderous combination of our town's hidden history, local lore, and unsolved mysteries that will leave you ruminating long after the tour has ended. Your entertaining local guide gives you a lay of the land and all the inside scoop on the harbor’s most mysterious unsolved death, Boothbay Harbor’s very own sea serpent, legendary treasure tales surrounding many of the harbor’s islands with a visit to the Boothbay Harbor Shipyard Museum where tall masted ships have been built for almost 200 years.

1. 1

   Stop 1

   10 min

   We’ll begin our tour in the heart of Boothbay Harbor at the town pier with beautiful harbor views of schooners, lobster boats, super yachts, and the harbor’s east side working waterfront. This town has always been a seafaring place, home to sailors and sea captains, fisherman, ship builders, and pirates!

2. 2

   Stop 2

   10 min

   What do Queen Elizabeth I, a ring, and Outer Heron Island have in common? Would you believe the claim on a $1 billion-dollar English estate?

3. 3

   Stop 3

   10 min

   Stroll along America’s longest wooden footbridge, enjoying spectacular harbor views, including Maine’s oldest lighthouse on Burnt Island with its long history of keepers—some who never left the island.

4. 4

   Stop 4

   10 min

   Originally built as a secret society lodge for the Knights of Pythias, the Opera House was saved from demolition with the help of two famous rock stars. It’s become an internationally renowned music venue and considered the most haunted building in Maine.

5. 5

   Stop 5

   10 min

   A mysterious stranger dressed all in black checked into the Hotel Fullerton and headed out for a glimpse of ocean surf. Her identity and untimely end are still unsolved mysteries almost 100 years later.

6. 6

   Stop 6

   10 min

   Local Wawenock leader Samoset became the first Indigenous person to contact the Europeans and sets an example for us today.

7. 7

   Stop 7

   15 min

   Visit the Boothbay Harbor Shipyard Museum and learn more about this historic shipyard where tall masted ships have been built for almost 200 years.

8. 8

   Stop 8

   10 min

   We wrap up back where we began with some classic seafarer superstitions and accounts of unknown creatures sighted by hundreds of respectable people up and down the Maine and Massachusetts coastline known as The Great New England Sea Serpent.

• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Not recommended for travelers with spinal injuries
• Not recommended for travelers with poor cardiovascular health
• Suitable for all physical fitness levels
• 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.