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Bob Crawford
How should we view Sybil Luddington's story with all that we do know about it and with all that we don't know about it?
Karen Romano Young
Well, I think we have to say that there's a lot of legend part of it and that legend always has a grain of truth in it and then it also has a grain of wishful thinking in it.
Bob Crawford
You've reached American History Hotline. You ask the questions, we get the answers. Leave a message. Hey there, American History Hotliners, Bob Crawford here. Thrilled to be joining you again for another episode of American History Hotline, the show where you ask the questions. And the best way to get us a question is always to record a video or a voice memo on your phone and email it to AmericanHistoryHotlinemail.com that's AmericanHistoryHotlinemail.com okay. Today's question comes to us from Greta in New Zealand. She writes, growing up in the US I developed a love of American history and recently I found out about the fascinating story of Sybil Ludington. She was definitely overlooked in the history books, in my opinion, and not given much credit. Would you consider doing an episode on her? Thanks so much and much love from New Zealand. Much love from the US Greta, and thanks for the suggestion. Well, joining me now to talk about Sybil Ludvington is Karen Romano Young. She's an author who wrote the book Sybil Revolutionary War Rider. Karen, thanks for joining me today.
Karen Romano Young
Hi. Thank you so much for having me.
Bob Crawford
We are thrilled to have you. And I am really excited to talk about this because there was a cartoon TV series that we just that that my wife and I discovered when my children were very young. I'm talking like you know, in the months old and like 1 year old. And it was called Liberty Kids. And I could not wait until they were old enough. We bought the DVDs. I think it came out in the 90s or early 2000s. The voices were like Charles Kuralt and Sylvester Stallone. It was like a star studded cast. And the main character, one of the main characters of this cartoon series about the Revolutionary War was none other than Sybil Ludington.
Karen Romano Young
What? Yes. I've never heard of it.
Bob Crawford
By a company named Cookie Jar. I can't believe you've never heard of this. You need to go immediately after we get off this conversation and order this series for yourself because you will absolutely love it. And this has formed my whole opinion and this is the scope of my knowledge of Sybil Luddington is based on this series, which I love to this day. And, yes, my kids eventually did grow into watching this series, and we watched it for many years, and now they're sick of it, and now they've outgrown.
Karen Romano Young
So, Aaron, these kinds of things make such a difference to kids. They give them what I call the hook of history, you know, just like, grab you with that hook and pull you into somebody else's reality that's been long gone, 300 years ago and make you. Make it come alive for you.
Bob Crawford
That's what we're trying to do here today. Fantastic goal of this show. That is the goal. We are on the same mission. Okay. So many people obviously don't know Sybil Luddington.
Karen Romano Young
Okay?
Bob Crawford
I've seen her referred to as the female Paul Revere. How does that characterization sit with you?
Karen Romano Young
I would rather say that Paul Revere was the male Sybil Luddington. You knew that was coming. Paul Revere himself has written. Well, did write a number of disclaimers and descriptors of what happened to him, you know, on the 18th of April in 75. And the way that Longfellow, who wrote the poem that made him famous, described that night is very different from the way Revere describes that night. For one thing, he only went so he was letting the people in Lexington and Concord know that the British were coming and that they were going to come and invade their towns and start the Revolutionary War. And they went 12 to 14 miles. There's just some debate there. He had a bunch of people helping him. Yes, somebody did look up in the old north church tower and see that there were two bells, one of by land and two of by sea. And then people did go off and say the British were coming. But it was on a far different scale from what Sybil Luddington did, what Sybil Ludington did. Her father was a colonel in a regiment of Patriot Minutemen, and they had just come back from a training expedition. And he sent all 421 of his soldiers home on furlough because it was springtime and they needed to plant their fields. Right after that, the British came marching in near where I live. I live in Bethel, Connecticut. The British came sailing up to the nearest shore, which is Westport, Connecticut, Campo beach, and they marched up into these hills to get to Danbury, which is just one town beyond where I live and where all the supplies were, and they burned Danbury, burned all the supplies, took what they wanted, got drunk on all the rum, and then they headed west to meet up with other soldiers that were in the Hudson Highlands. The Ludingtons lived in between. They could see the fires in Danbury from their houses. They knew that they needed to come and fight back the British, even though there were 421 of them and 2,000 of the British. So he needed to call those 421 men back in to muster and then to lead them on. But if he went himself to do it, Colonel Henry Ludington, he'd be exhausted by morning and he wouldn't be able to march off and do whatever he needed to do. So the question was who could ride and call out all the militia? And it was his 16 year old daughter Sybil who did it.
Bob Crawford
Amazing.
Karen Romano Young
This is an iHeart podcast.
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Bob Crawford
First.
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Bob Crawford
Were the Ludingtons always hardcore patriots?
Karen Romano Young
No, they were not. Henry Ludington was on the British side, the loyalist side, partway through the French and Indian War, and at some point he turned and moved over to the patriot side. So there was a bounty on his head and these kids grew up. Sibyl is the oldest of 12. The oldest three were girls. Boys were not old enough to be soldiers at all. These girls were old enough to be soldiers and they were on it in the way of eldest daughters, you know, really helping out their family. And they, you know, took care of the farming. They took care of everything that had to happen. When he was off fighting battles or training his men, they took care of their mom who had you Know, a baby in arms. And they even fought off the soldiers that came from the loyalist side to try to get the bounty that was on their father's head and were going to invade their house. These were some. I don't know if. Can I say badass on your show?
Bob Crawford
You could say badass. Yeah.
Karen Romano Young
Yes. So these girls are known for having helped out with, as everybody did. All of the militiamen were dressed in homespun. They did not have the beautiful red coats and the helmets and the, you know, the good equipment that the British soldiers had. They had to make everything themselves or come up with whatever muskets they could have. So they were working very hard to make coats for their militiamen. They were weaving, and all the women were dyeing all the material blue and cutting it and making it into these jackets, and they had this stuff all over the house. When somebody realized that there was a bunch of guys in the woods who were coming for their father, it was dusk. They lit some candles, and they put these coats on, and they walked around in front of the windows so that if you were outside in the woods, it looked like the militia were all there already. Yeah. This is the kind of girls they were.
Bob Crawford
So where does this come from? Like, was Henry Luddington. Did he just realize, like, this is what we have to do, and these are the people that we have to do it with are my daughters, and we're going to make this work, or what? Like, did they. Did he have to be convinced of their abilities? Like, do you know how this was accurate? Because this is contrary to this time period. Right.
Karen Romano Young
You might say, prove me wrong.
Bob Crawford
Yeah, tell me I'm wrong.
Karen Romano Young
To what we have heard about the time period. One of the really interesting things about this time period, and it's really borne out in this book, my book, is how much they relied on intelligence. George Washington was huge on this. He said, there's no way we're outnumbering these soldiers. The only way we're going to beat the British is through intelligence. We have to be ahead of them. We have to know what's going on, and we have to be sneaky. And along with John Jay, who was a big New York lawyer and who lived in the same area as the Ludingtons, Washington had spy rings that went all around New York City that involved women. There was one woman whose laundry hanging in her shoreside house, indicated where troops were and if it was safe to land and all this kind of thing, you know, we know her name, but we don't know the name of a whole lot of other women. So in this story, there is a slave girl who shares some intelligence. There is an older woman who is the mother of two young men who are in this militia, and she's. She's got a dog in the fight. She wants to help them out, and, you know, she goes to a mill in disguise and of some information along. And there's a whole lot of coding going on. Stuff that kids really love about this book is all the different methods for sharing messages that you could use. You know, whether you've got a letter that has a cutout on the front. You know, in the book, it's a valentine, so there's a heart cut out. And if you place the cutout over the letter, it has. It shows words that have a message. There's other ones where you have a particular book that you've got one and I've got one, and we've both gone through and put an underline on the page. Just randomly. It looks like somebody was taking notes. And all that anyone would get as a code was numbers. And they would know to go to the page in the book that they both had and see which word was underlined, and they would put a message together that way. So all of this stuff. And, you know, I grew up loving codes. I grew up writing letters. I grew up sneaking around and leaving messages under rocks and all this kind of thing that kids love to do. Girls love to do it just as much as anybody else. The fact that you were a girl in this time meant that. Yeah, you know, the classic thing where you're supposed to be home doing your needlework or whatever. While that may be true, that wasn't always possible. Girls had to go off and do lots of errands. They had to be in public a lot. And they were not. They didn't have such high expectations placed on them, so it was easy for them to slide under the radar a great deal.
Bob Crawford
What do we know about. You talked about three daughters.
Karen Romano Young
Yes.
Bob Crawford
So what's the birth order here? Where does Sybil Luddington fit in with her sisters? Is she the oldest? Is she in the middle? Where is she?
Karen Romano Young
She's the oldest.
Bob Crawford
She's the oldest.
Karen Romano Young
Okay, she's the oldest. So she's the big boss girl. And she has a sister who's a year younger, and then she has another sister who is. So they're 16 and 15. And I think Molly, the next one down is 11 or 12.
Bob Crawford
And was it her father's idea to send her, or did she. As far as we know. Did she convince her father that she had to do it, that she could do it, or did he say, sybil, this is what you need to do?
Karen Romano Young
Well, this is an interesting thing about Sybil Ludvington, is that we know she did this. We know how many people were in the militia. We know it all happened on one night. We know it took 40 miles. We even know the route that she took, but we don't know all of the particulars of it. We don't know if she said, you know, I can't. You know, I regret that I only have one life to give for my militia, you know, or something like. Yeah.
Bob Crawford
Was there a rallying cry? Do we know that she had a rallying cry?
Karen Romano Young
Well, she said, you know, muster Luddingtons. The British are coming. Yeah. And, you know, that was the message. You all have to come down and get together, and we're all going to march off. But we don't know enough about her in this particular instance. What we do know about her comes from other stories about her, such as this thing where she and Becky and Molly and the mom put the militia coats on and pretended that the house was full of guys and that they shouldn't come invade them. We know that she could light a campfire in the woods by shooting a musket.
Bob Crawford
Wow.
Karen Romano Young
Which is the kind of thing, you know, it's kind of like I've, you know, learning to spin a basketball on one finger.
Bob Crawford
Yeah.
Karen Romano Young
You know. You know, the cool girls can do this. They had to learn how to use muskets. They had to go out and hunt. Right. Just like anybody in this time was. Would go out and hunt for, you know, little creatures for. For dinner. And she also had to have knowledge of a musket because of the situation in the territory where it was just loyalists on one side and patriots on the other side and, you know, people who are pretending to be one thing to fool the other side and going back and forth, and spies who were double agents pretending to be loyal to one side but secretly spying on everyone. And a lot of this stuff was going on. You had people called cowboys, two words. And Skinners who would go around and steal livestock and then sell it back to you, you know, and sell your identity to. And tell people they were going to tell you, tell the folks you were a loyalist if you didn't pay to get your livestock back. So you needed a musket. There was a lot of going on.
Bob Crawford
Right. So. So do. Do we know, like, what happens after this battle? Like, did the militia win this, this, this showdown with the British?
Karen Romano Young
Well, yeah, so I've already told you how they marched in and they went to Danbury and they got good and drunk and they were up all night and they were going to go and march over toward the Hudson Highlands and meet up with another regiment, you know, wreak all kinds of havoc. But they were met by Ludington's troops and so they went back a different way. They got pinned down. They were, you know, the British marching along and these soldiers were outnumbered and they were up in the trees and, you know, shooting horses out from under people and things. And in the end they chased the British all the way back to the beach and, you know, boat came along and picked them up and they got away. But there was no more going across New York and meeting up with the other guys.
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Bob Crawford
This is American History Hotline. I'm your host, Bob Crawford. Today my guest is Karen Romano Young. She's an author who wrote the book Sybil Revolutionary War Rider. Remember to send us your burning questions about American history. Record yourself using the voice memo app on your phone and email it to AmericanHistoryHotlinemail.com that's AmericanHistoryHotlinemail.com now back to the show. Okay, so regardless of, like, the truth of what she did and everything we know about it and the things we don't know about it, when does the story of Sybil Luddington start to become popularized?
Karen Romano Young
Not for a long time, Bob.
Bob Crawford
Okay.
Karen Romano Young
Well, Sybil went on after this and married a soldier and had a son and ran a tavern and for various reasons died in poverty because her husband was not able to. When he died, she was not able to pick up his pension because she couldn't. She didn't have a marriage certificate. They had moved around.
Bob Crawford
Let me ask you this.
Karen Romano Young
Yeah.
Bob Crawford
Was she involved in any other battles or any other excurs, like any during the war after this? Was she. Was she further involved in the war? You say she married a soldier.
Karen Romano Young
She married a soldier. We don't know. The only way that we know anything about Sybil, this is a really important distinction. It wasn't talked about right after it happened. She didn't become a big hero. You know, she wasn't given some kind of award for loyalty or for speed on a horse or anything like that. It was kept very quiet. And I'll go back to why in a minute. But it was something along with the musket starting a fire along with the soldiers trying to get the bounty that was on the head of her father. Family stories. And in 1907, Henry Ludington's grandson, Lewis Patrick, went to a writer and said, I want the memoirs of my grandfather published. I want to tell you what I know about him and the rest of his family, because it's about to be lost to posterity. It hadn't been written down. There are a lot of historical documents and things. There is a story or an account of the Battle of Ridgefield, which was when they fought the soldiers back. There are clear accounts of the British coming and marching in and burning Danbury and all of that. But there wasn't very much about Sybil at all until this memoir was published. Because this grandchild, this grandson, remembered the stories that the family had told about Aunt Sybil, and he wanted her story remembered. And at that point, the Daughters of the American Revolution picked it up and started to share it around. In 1935, they put up marker signs all along her route. And when Anna Huntington, who was a sculptor who lived in this area, daughter of one of the railroad magnates who lived in this area, became A sculptor and wanted to do a sculpture of some famous patriot in this area. She heard about Sybil Ludington. So my kids grew up going to the Danbury Public Library and seeing her statue of Sybil in front of the library. She's on a horse coming down a hill, and her hair is streaming behind her, and she's screeching, you know, muster at Luddington's. The British are coming. And my kids just said, who is that? And I didn't know. So, you know, that's how I found out is from this statue in 1975. They did a postage stamp about her. Just. They all started to find out this story, but so little is known, and there were so many lurid kind of tales told. You know, her horse was named Star, and she rode in a dress. No, she rode in breeches. Her hair was streaming behind her. No, she had it pulled up. And she was disguised as a man. Nobody knows. Nobody has any idea. Some say she said, I father must drop, you know, must jump on that horse and ride through the night, you know. And some said, no, I need you to do this, kid. Or, you know. Others said she was one of six people who was supposed to, like, do it in a chain. And she just took it over and did the whole thing. Nobody has any idea. What's interesting to me is to say, why didn't they talk about it at the time? And I think that the reason they didn't talk about it at the time was the reason that they didn't talk about a lot of women at the time. Women did all kinds of things. Their sons and daughters were on the line in this situation. They were trying to, you know, have freedom for their country just as badly as the men were, even if they weren't personally able to put their lives on the line. Although I believe that they did. I just think that a. Historians don't go looking for those little stories. They write about battles and they write about the colonels, and they write about the, you know, people whose names are on the list. It's very easy. It's very easy to go back and find every single person who is in this regiment down to the lowliest fife boy. But could you find anything else about their families? No. So there's a lot we don't know. And that's where the fascination of this whole tale came in, was coming up with who else lived in the area that they were worried about and who else lived in the area like the Quakers, who were allies. And it was fascinating to come up with once you knew the parameters of the story were to kind of go, well, what might have happened? Let's make this a good story that seems to be going along with the character that we know that this person had, which is independent and fierce and strong and a badass boss girl.
Bob Crawford
Thinking about this area that you're talking about, one name comes to mind and just. Was he. Am I right in thinking Benedict Arnold also came from this area?
Karen Romano Young
He was. They called out a number of different regiments to fight the British back. Benedict Arnold came from New Haven and brought his men with him. He did not turn coat until after this.
Bob Crawford
Right. But he knew Henry Ludington, we can
Karen Romano Young
assume, or at least he's that guy over there running that bunch of guys, and I'm over here running this bunch of guys. At least that much. Yeah.
Bob Crawford
So you know what you're just talking about. I get conflicted as a historian. On the one hand, I want the cold, hard facts, but I also understand the value of a good American story, especially one that includes female heroism and gets. And like you said, the hook of history gets kids interested, pulls people in. How should we view Sybil Luddington's story with all that we do know about it and with all that we don't know about it?
Karen Romano Young
Well, I think we have to say that there's a lot of legend part of it, and that legend always has a grain of truth in it, and then it also has a grain of wishful thinking in it. And you can see that if you go through. I worked a lot with the Putnam county historian, Sally Cipher, who had a lot of opinions about this and who shared with me old copies of all these articles that came out, you know, between the 30s, 40s, 50s, 60s, 70s, when she was starting to come back into the limelight, and people just wrote all kinds of, you know, whatever appealed to them about this story to fill in the spaces. I did the same thing. You know, there's no other way to do it other than to try to fill in the spaces. So when it says based on a true story, all the facts that we know are there, but what else? And it was very fun to do this story because I live in the area, right out and follow her path. We drove where their family's home used to be, where their mill used to be, and we looked across the fields and there, sure enough, you can see the steeples of Danbury and, you know, right near the public library where the statue is. And then we could. We rode through the whole countryside and just imagined. And it says there was An Indian village, you know, up that road. That's interesting. They're not there anymore, you know, and. Or are they? And have just assimilated. Where were the houses of the militiamen? And what are all these other houses that are between them? Are they all loyalists? Are they people that don't have men of fighting age? You know, so you just kind of have to figure it all out going along. It's fun.
Bob Crawford
What do your kids think of the book?
Karen Romano Young
Well, my oldest, who is an American girl from way back with her American Girl dolls and who just has an incredible imagination, drove this route with me and pointed out a whole lot of things that I didn't figure out on my own, and even things like, okay, we've done the whole route, now we're going to take the shortcut back to Bethel. We're driving on Quaker Hill Road. Why is it called Quaker Hill Road? I went and looked that up because that's where all the Quakers lived. And it's a very. It's the road between here and there that would have been a secret little passage to go through. And nobody's suspecting the Quakers of anything, but they might just be passing messages along. They might just show up with a horse when yours is exhausted on your ride. And that's how I got the horse to be called Star, even though I wasn't going to go along with the apocryphal story that her horse was called Star. Yeah. So.
Bob Crawford
Well, your assignment, Karen, if you choose to accept it, is to look up Liberty Kids.
Karen Romano Young
I will.
Bob Crawford
And watch the whole series. And then we will reconvene and we will debrief.
Karen Romano Young
That would be great. I think that's incredible that I didn't know about that. That's funny. And I bet Sally Cipher doesn't know either.
Bob Crawford
It is just tremendous. I personally love it. And there's some apocryphal parts of it, I'm sure.
Karen Romano Young
Yeah, they pick up on stuff like that. But I mean, as you're going forward and you're hearing about God, girls and women doing things, you know, it's not just think about how their stories were hidden, but think about what they brought to the situation. What kind of skills did they have that the boys might not have had? You know, even if it meant I can slip through this whole group of people and nobody thinks I know anything and I can pass a message along
Bob Crawford
and, you know, well, we always need to remember of that time what Abigail Adams said to her husband. Remember the ladies.
Karen Romano Young
Remember the ladies, Absolutely. Yes.
Bob Crawford
I've been talking to Karen Romano Young. She's written many books, including Sybil Luddington, Revolutionary War Rider. Check out her entire catalog online. She's got a ton of great books. Karen, thanks for joining us on American History Hotline.
Karen Romano Young
Thank you so much, Bob. It's been a pleasure. And thank you to Greta in New Zealand. I'd love to know if you lived around here and saw that statue too.
Bob Crawford
You've been listening to American History Hotline, a production of iHeart podcasts and Scratch Track Productions. The show's executive producer is James Morrison. Our executive producers from iHeart are Jordan Runtal and Jason English. Original music composed by me, Bob Crawford. Please keep in touch. Our email is americanhistoryhotlinemail.com if you like the show, please tell your friends and leave us a review in Apple Podcasts. I'm your host Bob Crawford. Feel free to hit me up on social media to ask a history question or to let me know what you think of the show. You can find me at bobcrawford Bass. Thanks so much for listening. See you next week.
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Karen Romano Young
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Host: Bob Crawford
Guest: Karen Romano Young, author of Sybil: Revolutionary War Rider
Release Date: March 18, 2026
This episode explores the legend and historical reality of Sybil Ludington—a 16-year-old whose daring midnight ride during the American Revolution has often been compared to Paul Revere. Responding to listener Greta from New Zealand, Bob Crawford and guest Karen Romano Young dive into what we know and don’t know about Sybil’s story, its place in American memory, and the wider role of women in Revolutionary-era intelligence and resistance.
| Timestamp | Segment | |-------------|--------------------------------------------------------------| | 00:00–01:43 | Introduction, listener question from Greta, guest intro | | 03:36–06:53 | Comparing Sybil Ludington to Paul Revere, detailing the raid | | 10:44–13:00 | The Ludington family, girls in the revolution | | 13:26–16:38 | Spies, intelligence, and coded messages | | 19:47–20:48 | Aftermath of the ride, battle outcome | | 25:25–26:08 | Sybil's post-war life and story’s delayed recognition | | 29:36–31:25 | The omission of women in recorded history | | 32:33–34:26 | Legend vs. fact, crafting the narrative | | 36:27–36:35 | “Remember the ladies”—closing reflection |
This episode compellingly highlights how Sybil Ludington's ride, once obscure, is now embraced as a symbol of youthful courage and women’s overlooked contributions to the Revolution. Crawford and Young strike a balance between honoring the legend and acknowledging the limitations of historical evidence, reminding listeners that stories—especially about extraordinary women in history—matter for both their factual and inspirational power.