In Episode 413 Jeff Belanger and Ray Auger explore the woods of Great Chebeague Island in Casco Bay, Maine, searching for an old cellar hole that’s said to be haunted by the ghost of a slain pirate who still guards hidden pirate treasure. Multiple witnesses over generations reported strange happening in and around this spot.
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CREDITS:
Produced and hosted by: Jeff Belanger and Ray Auger
Edited by: Ray Auger
Theme Music by: John Judd
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EPISODE TRANSCRIPT:
*A note on the text: Please forgive punctuation, spelling, and grammar mistakes. Like us, the transcripts ain’t perfect.
[OCEAN SOUNDS / SEAGULLS]
RAY: We’re in the final minutes of summer, Jeff. Still… not a bad day to be out here on Great Chebeague Island, off the coast of Maine.
JEFF: Not bad at all, but yeah, you can feel there’s just that slightest chill in the air. We know Autumn is just around the corner, and the tourists will thin out until it’s just the few hundred people who call this island home year round.
RAY: There IS a bit of a chill today.
JEFF: It’s going to get chillier, Ray. We’re going to head a little inland.
RAY: Okay… what are we looking for?
JEFF: We’ve come to Great Chebeague Island searching for pirate treasure, a ghost, and a haunted cellar.
[INTRO]
JEFF: I’m Jeff Belanger.
RAY: And I’m Ray Auger, welcome to Episode 413 of the New England Legends podcast. Thank you for joining us on our mission to chronicle every legend in New England one story at a time. We’re always on the hunt for ghosts, monsters, aliens, roadside oddities, eccentrics, and all other weirdness that makes this place great. Most of our story leads come from you, so please reach out to us anytime through our website.
JEFF: Thank you to everyone who has already purchased my brand-new book Wicked Strange New England featuring the photography of Frank Grace. The feedback so far has been amazing! It’s on sale now wherever books are sold. And our new 2026 Haunted New England calendar is also out now! You can find a link on our website. We’ll go searching for pirate treasure and ghosts right after this word from our sponsor.
SPONSOR
RAY: Pirate treasure AND ghosts… it doesn’t get better than that.
JEFF: No it doesn’t. Let’s set the stage here.
RAY: Right. Great Chebeague Island is one of hundreds of islands in Maine’s Casco Bay. It’s also the largest.
JEFF: Thus the Great part of the name.
RAY: Exactly. The name is from a Wabanaki word that roughly translates to “Island of many springs.” During the summer months the Native people would come here to fish and gather shellfish, and they would leave in the colder months. The island was first settled by colonists in 1746, and from there it grew as mostly a fishing and farming community. But they also manufactured stone sloops—ships that would carry granite from quarries down the eastern seaboard to help construct lighthouses, breakwaters, and things like that. The whole island is about 25 square miles. Chebeague was part of the town of Cumberland right up until 2007 when it broke off and became its own town.
JEFF: Today the island is the year-round home to just under 400 people, though that can triple in the summer.
RAY: Being September we’re mostly left with the locals. And locals have stories.
JEFF: That they do.
[WALKING IN WOODS]
JEFF: We’re on the eastern side of Great Chebeague Island heading into Littlefield woods. Behind us we can see Crow Island just offshore from the big island. What we’re looking for today is only a cellar hole… a haunted cellar hole. To find out why, let’s head back to the year 1939.
[TRANSITION]
RAY: It’s September of 1939 here on Great Chebeague Island. The nights are getting cooler, America is still in the Great Depression, but thankfully folks here can still fish for their suppers. But the big buzz around the island these days is a haunted cellar. Just a cellar hole now, but it used to be the Webber family home above it long ago.
JEFF: Before we get to the cellar, we should give you a little more backstory on why locals suspect it’s haunted. We know pirates roamed these waters. Some even suggest none other than Captain Kidd himself was up this way.
RAY: New England waters were full of pirates. We had busy ports with ships coming and going, and that’s where pirates plied their trade.
JEFF: That’s true. And we know pirates would bury treasure in various places—especially if they were being hunted down. If their ships were raided, it was a good idea not to have all of the treasure in one place.
RAY: Right. So bury the treasure in various locations and go back and get it later.
JEFF: Get it later unless they get caught and then the treasure is left behind if everyone who knows where it’s buried is hanging at the end of a rope.
RAY: Exactly.
JEFF: There’s a story they tell here on the island about folks searching for buried pirate gold in Casco Bay. A story that’s been passed down through the generations. Over on Richmond’s Island just south of here, not that long ago a farmer was plowing his field and unearthed some gold coins. Jewell’s island is another spot where they say Captain Kidd buried treasure. So it’s no stretch to believe Chebeague Island might have its own riches. In fact, there’s a man on Cliff Island who will testify that a stranger and his friend once rowed his boat over to Cliff Island and hired him to row over to Hope Island and dig for treasure. He claims they unearthed a sealed iron pot that jingled with coins when struck. They couldn’t unearth the pot or pry the lid off with the tools they had, so the stranger sent his friend back to fetch more tools. The following morning, the pot, the stranger, and his friend were gone.
RAY: So plenty of evidence of buried treasure in this region.
JEFF: That’s for sure. Let’s head through the field to see the place.
[WALKING IN WOODS]
JEFF: It’s not much to look at, is it?
RAY: No, not really. Just a large depression in the ground with weeds and shrubs growing out of it now. But this is the place?
JEFF: This IS the place. Something strange happened here. And when you hear the stories, it’s easy to imagine the ground is hungry for something… or hiding something… and if you get too close. Who knows.
RAY: Maybe we should back up a couple of steps.
JEFF: Maybe. Mrs. George Leonard told me that she heard from both her mother and grandmother who knew the Webbers when they lived in the old house over this haunted cellar. The story goes, one evening the Webbers heard a strange sound coming from their cellar.
[TAP TAP TAP in the distance]
JEFF: Just a tap. Maybe a rodent or animal had found its way into the cellar.
[TAP TAP… TAP]
JEFF: But there it was again. So they decided to investigate.
[DOOR CREAKS OPEN]
JEFF: When they opened the cellar door, there stood a pirate standing in their basement staring blankly back at them, with blood running from his recently slit throat.
[DOOR SLAMS]
[WOMAN SCREAMS]
JEFF: They screamed.
[RUNNING FOOTSTEPS]
JEFF: They ran from the house. And took some time outside to gather their courage again to go back in. Once they did, they opened the cellar door.
[DOOR CREAKS OPEN]
JEFF: And saw an empty cellar. No sign of anyone having been there.
RAY: That gave me chills. I can’t imagine seeing a site like that. We know from exploring other stories of hidden pirate treasure that sometimes a pirate captain would bring a crewman along on shore to dig the hole to bury the treasure. Once the hole was dug and the treasure secured, the pirate captain would sometimes make sure the location remained hidden in a most lethal way.
JEFF: Yeah…
RAY: Dead men tell no tales. And then the poor crewmen’s cursed spirits are tied to the treasure forever.
JEFF: That’s the conclusion folks on Great Chebeague Island reached… maybe there’s buried treasure in or near that cellar, and this was the poor pirate who had to dig the hole.
RAY: I was speaking with another local named Henry Bowen who said his mother once worked in the old Webber house. She used to hear the most frightening sounds.
[LOUD BANGING ON THE SIDE OF THE HOUSE]
RAY: She told me it was as if someone hit the side of the house with a club. The sounds would go on, but no one was ever found outside… No one living anyway.
JEFF: Mrs. Clifford Leonard said she recalls her Great Uncle William Littlefield telling her back around 1850 he once saw pirates carrying a chest across his field and walking down to the harbor. He gathered some men and followed their footprints through the wet grass. It led them by the old cellar hole.
[WIND BLOWS BY]
JEFF: A strange wind began to blow…
[HORSES GALLOPING]
JEFF: They heard horses galloping all around them, but no sign of any horses. Just sounds on the wind.
RAY: Other locals will tell you they still hear those disembodied horses to this day.
JEFF: For many years no one could seem to live in the house over the haunted cellar very long. Finally, the house was moved to another part of the island and all that remained was the cellar hole. But the haunting continued. The kids would avoid walking by the cellar hole because of the stories of ghosts and pirates.
[FAINT HORSE GALLOP IN THE DISTANCE]
RAY: Do you hear that?
JEFF: I do… they say those pirates never found all of the buried gold, and as long as there’s still some in the ground, the spirits here will never be at rest. And that takes us back to today.
[TRANSITION]
RAY: Today the grounds on this part of the island are covered in forest. People still hike through, but the stories are so far in the past, it’s just legend now.
JEFF: Most of what we know about this haunting comes from Eleanor Troy Williams’s article in the January 7, 1939 Lewiston Sun-Journal. She named names and shared the stories.
RAY: The assumption is that the cellar hole was about the spot where pirates once buried treasure.
JEFF: That’s the story and the folks of Great Chebeague Island are sticking to it.
RAY: The golden age of pirates was considered from the mid sixteenth to the mid-seventeenth century. That’s not to say there weren’t some pirates still around in later years, but the governments of the world made it their business to hunt down pirates because it was devastating to shipping and commerce.
JEFF: They did, and then the locations of the buried treasure either spread through old maps, or legend. While we can’t prove pirates buried treasure on Great Chebeague Island, enough locals believed it to the point they used those scallywags as the source…. for their haunted cellar.
[OUTTRO]
RAY: And that takes us to After the Legends where we dig a little deeper into this week’s story and sometimes veer off course.
JEFF: After the Legend is brought to you by our Patreon patrons! This group is the best. We can’t bring you two podcasts each week without them. We’d love it if you’d join us over there, where you’ll get early ad-free access to new episodes, plus bonus episodes and content that no one else gets to hear. It’s just $3 bucks per month, but it goes a long way in helping with our expenses. Great content isn’t free. So thank you to our patrons. To sign up head to patreon.com/newenglandlegends.
To see some pictures of Great Chebeague Island click on the link in our episode description or go to our website and click on episode 413.
Before we part ways today, please make sure you’ve subscribed to our podcast wherever you get your podcasts so you don’t miss a thing. It’s free, and we love having you along with us each week. You can also help by posting a review, and telling your friends about our show. That’s how we grow and then more people share their weird tales with us.
We’d like to thank our sponsors. Thank you to our patreon patrons, and our theme music is by John Judd.
Until next time remember… the bizarre is closer than you think.