Podcast 224 – Dr. John Wilson’s Dark Secrets

In 1821, Dr. John Wilson designed the Round Schoolhouse because he wanted to be able to look out in all directions in case someone came looking for his secrets.

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In Episode 224, Jeff Belanger and Ray Auger go back to school when they search for the Round Schoolhouse in Brookline, Vermont. The school building was designed in 1821 by Dr. John Wilson who wanted the building round so he could look out the windows in all directions in case someone comes looking for him… because Dr. Wilson is a man with secrets. Dark secrets that he took almost to his grave.

Read the episode transcript.

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Produced and hosted by: Jeff Belanger and Ray Auger
Edited by: Ray Auger
Theme Music by: John Judd

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The Round Schoolhouse on Grassy Brook Road in Brookline, Vermont.

The Round Schoolhouse on Grassy Brook Road in Brookline, Vermont.

Dr. John Wilson aka John Doherty aka Captain Thunderbolt

Dr. John Wilson aka John Doherty aka Captain Thunderbolt

*A note on the text: Please forgive punctuation, spelling, and grammar mistakes. Like us, the transcripts ain’t perfect.


RAY: There’s not much up here in Brookline, Vermont, is there?

JEFF: No, it’s kind of rural. We’re driving north on Grassy Brook Road which runs through this pretty valley.

RAY: We’ve passed a couple of small farms. And a few houses, but it’s pretty spread out here, what are we looking for?

JEFF: Ray, I hope you brought your pencil and notebook this week, because we’re going back to school. We’re searching for a building along this road called Round Schoolhouse.

RAY: Okay, I’ll keep my eyes peeled…


RAY: Yeah…. That’s pretty much impossible to miss.

JEFF: You’re right. There’s no question we’ve arrived.


RAY: It’s not a very big building, but it’s completely round with a cone for a roof. It’s made of bricks, and there’s an attached barn next to it.

JEFF: This is our destination. Back in 1821, Dr. John Wilson who was not only the town doctor, but also the town school teacher, had this schoolhouse built to his specifications.

RAY: Why did he want the building completely round like this?

JEFF: Because Dr. Wilson was scared someone may come looking for him, and he needed to be able to lookout in any direction. Because Dr. John Wilson was a man with dark secrets…


JEFF: Hello, I’m Jeff Belanger, and welcome to episode 224 of the New England Legends podcast. If you give us about ten minutes, we’ll give you something strange to talk about today.

RAY: And I’m Ray Auger. Thank you for joining us on our mission to chronicle every legend in New England one story at a time. We love being part of your day, and are grateful to have you riding along with us. We’re a community of legend seekers who love sharing these strange stories that make our region unique.

JEFF: Ray… this past week our podcast hit a milestone.

RAY: What’s that?

JEFF: Four million downloads and counting!

RAY: Four million?!

JEFF: Four million! So if you don’t already subscribe to our podcast, please do. You can download and subscribe for free wherever you get your podcasts so you won’t miss a thing. Also be sure to check out the New England Legends television series on Amazon Prime.

RAY: Before we try to uncover the dark secrets of Dr. John Wilson, we want to take just a minute to tell you about our sponsor, Nuwati Herbals!

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RAY: And because I DO want to have those extra treats this month, I’ve been drinking Honey and Spice tea from Nuwati Herbals. It’s a sweet afternoon treat, and if you want to kick it up a notch, go ahead and dip a candy cane in there while you stir to add a little peppermint flavor. Nuwati Herbals has a ton of great products that make great holiday gifts.

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RAY: Okay, Jeff, the Round Schoolhouse in Brookline, Vermont, is well named.

JEFF: It is.

RAY: This brick building has stood for 200 hundred years, and it really stands out. I mean, I’ve passed other historic, one-room school buildings that still stand today. There’s often an historic plaque out front to mark them. But they don’t look like this. We’ve even covered the story of the haunted one-room schoolhouse in Newburyport, Massachusetts, back in Episode 181. Remember that?

JEFF: That’s right!

RAY: But those buildings were all rectangular. And you’re saying there’s a secret reason that this one is round?

JEFF: That’s what they say… so let’s head back to 1821 and meet Dr. Wilson a man with secrets.


JEFF: It’s the Spring of 1821, and a tall, handsome stranger with a Scottish brogue has just arrived in the small town of Brookline, Vermont. He’s just moved from Dummerston, just about 10 miles to the south of Brookline. He tried to operate a medical practice there, but there wasn’t enough business. So he’s moved north.

RAY: Brookline isn’t much bigger than Dummerston. I’m not sure he’ll do much better here.

JEFF: Dr. Wilson understands that, so he offers to be the town doctor AND teach the kids their schooling. And that sounds pretty good to the people of Brookline.

RAY: Meanwhile, some of the Brookline locals ask those get-to-know-ya questions of Dr. Wilson. When they do, they find he’s not too forthcoming. Wilson claims he was a medical doctor in his native Scotland, that he arrived in Boston three years ago in 1818, and tried to make a go of his practice in Dummerston.

JEFF: And that’s about all the good doctor will offer. He’s cagey when it comes to talking about himself, other than studying at medical school. He’ll go on and on about the beauty of the English countryside and things like that, but when discussion turns to himself, he shuts it down. And then when the town agrees to construct a schoolhouse for him, people grow more suspicious when Dr. Wilson insists on a specific design for the building: he wants it round, with windows facing in each of the cardinal directions.

RAY: Still, the town builders shrug, and get to work.


RAY: And pretty soon, Dr. Wilson’s Round Schoolhouse is complete and filling up with students.

JEFF: Wilson teaches his classes, but sometimes he’s distracted by looking out the windows. Considering the building is so close to the long, straight road, he has a good view in pretty much every direction.

RAY: Dr. Wilson is an impressive and worldly man. He can discuss things he’s seen in England and Europe, of course his background in medicine. He’s the kind of guy to get invited to local dinner parties. He’s a doctor, he’s smart, and an eligible bachelor after all, but every time the discussion turns to his own past, where he’s from, and his upbringing, the good doctor quickly changes the subject.

JEFF: Another curiosity about Dr. Wilson, is that shortly after moving into his Brookline home, he has a local carpenter build something strange.


JEFF: He builds a hidden compartment into a closet. Kind of like a false wall. It’s just big enough for him to get inside and hide. The carpenter asks who would need such a space, but perhaps a few extra dollars is enough to quiet the questions. Not the wondering, but at least the carpenter knows better than to press the matter.

RAY: When offered tea, Dr. Wilson grows agitated and demands coffee instead… because, of course, the British drink tea. Another curiosity about this strange man is when he walks into a room with various chairs, he always picks the chair in the corner so no one can sit behind him. If there isn’t a chair in the corner… he moves one there. It’s obvious this is a man with secrets.

JEFF: Then there’s the cravat he wears around his neck.

RAY: What’s so strange about that? Lots of men wear them these days.

JEFF: True, but Dr. Wilson’s cravats are extra large and frilly, and he even wears them on the hottest summer days. Plus, another strange things about him… Being an eligible bachelor, he gets asked to dance at parties, but he mostly refuses. He claims he’s clumsy. He also drinks quite a bit, so if he wasn’t clumsy before, after knocking back a few whiskeys, he’s stumbling now.

RAY: Dr. Wilson leaves Brookline after only a couple of years and makes his way on to Brattleboro, Vermont, where he continues his medical practice, AND his strange ways. He even marries a local girl, but she soon divorces him for being so abusive.

JEFF: It’s early March of 1847, when John Wilson becomes gravely ill. When a doctor arrives to tend to him, Wilson is lying in his bed fully clothed, including his fluffy cravat around his neck. The physician asks to loosen John’s clothes to examine him, but John refuses. He seems to know his end is near and he asks his physician to promise to bury him in these clothes – as-is. The doctor reluctantly agrees.


RAY: Dr. John Wilson draws his last breath on March 2nd 1847. He’s 57 years old… The doctor, though, can’t quite keep his promise. To prepare John Wilson’s body for a funeral, he needs to strip the man, and clean him up. As the physician removes John’s fancy cravat… a slew of secrets start to reveal themselves.

JEFF: Oh wow… look at that scar!

RAY: John Wilson has a big scar running a quarter of the way around his neck. I guess that’s why he wore the ties – to hide it.

JEFF: Right.

RAY: After pulling off John Wilson’s pants, the physician notices one of Wilson’s legs is shriveled. There’s a clear bullet wound scar in his calf, and the man has no heal. It looks like it’s been shot off. Instead of a heel, there’s a piece of cork.

JEFF: No wonder the guy had no sense of balance!

RAY: It turns out, John Wilson has several scars from wounds that look like knives and gunshots. The attending physician now suspects that John Wilson was hiding these scars and acting so strangely, not because he was vain… but because he had secrets.

JEFF: So the physician reaches out to the local sheriff, who agrees, this does sound strange. After searching his list of wanted criminals the sheriff discovers that Dr. John Wilson DOES match the description of Captain Thunderbolt – a Scottish highwayman whose real name was John Doherty.

RAY: After doing some more research, the sheriff learns that John Doherty would rob wealthy travelers on the roads of Ireland and Scotland. His quick getaways earned him the nickname, Captain Thunderbolt. An honorable thief, he would never rob from the poor or from women, which turned him into a bit of a folk hero.

JEFF: John Doherty continued his life of crime and eventually took on an Irish assistant named Michael Martin. The two men became partners, Captain Thunderbolt and Captain Lightfoot. The two had many adventures together, some of which lead to one or both of them getting wounded by their angry victims. The crazy thing is, John Doherty seemed to have a knack for surgery and medicine.

RAY: So he never went to medical school?!

JEFF: Never. He just did what he needed to do. Pretty soon, the pair figured out they could charge people money for his medicines and surgeries. But when the heat got too hot in Scotland and England, the two gathered up their riches, split up, and sailed for Boston a few months apart from each other. Once in Massachusetts, Michael Martin continued his life of crime from 1818 to 1821 when he’s captured, where he writes his confession, including the part where he mentions that he and Doherty parted ways because Doherty intended to change his name and live an honest life, while Martin continued his life of crime right up until his hanging. Martin’s confession goes on to say that Doherty is a master of disguise, with a knack for medicine.

RAY: No wonder Dr. John Wilson was always so nervous. Anyone who read the published confession of Michael Martin, knew that Captain Thunderbolt was now somewhere in New England.

JEFF: He was until his recent death when all of his secrets were revealed. And that brings us back to today.


RAY: Imagine living a secret life like that? Being scared all the time?

JEFF: I can’t imagine the stress that would cause. I love stories like these because those were times when you really could walk away from your life, give yourself a new name, even a new profession, and boom, you’re no longer John Doherty aka Captain Thunderbolt, you’re Dr. John Wilson, part-time school teacher.

RAY: I don’t think anyone could pull that off today. It’s not so easy to disappear anymore.

JEFF: One thing that hasn’t disappeared is the old Round Schoolhouse. It’s still here right off the side of Grassy Brook Road in Brookline. The funny thing is, does a round building really offer you more vantage points out the window than a square building with windows on each wall?

RAY: Good point. I’m not really sure.

JEFF: Either way, the Round Schoolhouse is a direct connection to Dr. John Wilson, and all of the secrets he took almost to his grave.

RAY: Almost to his grave if not for a meddling doctor who just had to know what was under that scarf. But are we sure Dr. Wilson was indeed the highwayman, Captain Thunderbolt?

JEFF: Not totally sure. Captain Thunderbolt’s partner, Michael Martin wrote in his confession that in Scotland, Doherty would act as a doctor, and he was his assistant. He described Doherty by height and a few other characteristics that do match Dr. Wilson. When the two decided to go their separate ways, Doherty claimed he hoped to die a repentant and honest man.

RAY: The descriptions of Dr. Wilson don’t make him sound too pious. He was a drunk, he abused his wife, and always seemed to be looking over his shoulder because he knew his secrets could one day catch up with him. Eventually… they did.


JEFF: Secrets do have a way with catching up with us. Here’s the worst-kept secret out there: We deeply appreciate our Patreon patrons! These folks are the backbone of everything we do. For just $3 bucks per month they help us with our production, hosting, and marketing costs, and they get early access to new episodes, plus bonus episodes and content that no one else gets to hear. Just head over to patreon.com/NewEnglandLegends to sign up.

RAY: Be sure to subscribe to our podcast, post a review, and share it with your friends. So many of our story leads come from our community. We love it when you get more involved. And we love hearing from you, whether through our Web site, social media, or our super-secret Facebook Group.

JEFF: We’d like to thank our sponsor, Nuwati Herbals, and our theme music is by John Judd.

RAY: Until next time remember…. The bizarre is closer than you think.

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