Podcast 162 – The Bootlegger Queen of Vermont

In Episode 162, Jeff Belanger and Ray Auger travel back to 1925 in West Halifax, Vermont – the height of prohibition – to ride shotgun with Hilda Stone, the Bootlegger Queen of Vermont, on one of her many runs to Canada. Stone was drawn into a life of crime after her husband came into financial difficulties, but she stayed for the love of the chase. Stone became an icon in the newspapers, and got arrested more times than you can count on one hand. But she kept coming back to deliver illegal booze to New Englanders.

Read the episode transcript.

(617) 444-9683 – leave us a message with a question, experience, or story you want to share!


Produced and hosted by: Jeff Belanger and Ray Auger
Edited by: Ray Auger
Additional Voice Talent: Michael Legge
Theme Music by: John Judd

Apple Podcasts/iTunes | Google Podcasts | Spotify | Pandora | Stitcher | Amazon Podcasts | TuneIn | iHeartRadio | SoundCloud

New England Legends Facebook Group

Hilda Stone - The Bootlegger Queen of Vermont - image from the Feb. 11, 1926 Minneapolis Star newspaper.

Hilda Stone – The Bootlegger Queen of Vermont – image from the Feb. 11, 1926 Minneapolis Star newspaper.

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


RAY: Wow! Car 23 is taking a commanding lead in this race!

JEFF: Yup, he’s really haulin’ the mail.

RAY: And I love the name of this racetrack here in West Haven, Vermont: Devil’s Bowl Speedway.

JEFF: It’s a good name.

RAY: Is it related to this week’s legend? Some devil creature from around here or something?

JEFF: The track isn’t related to the story, but these race cars sure are.

RAY: How so?

JEFF: If not for a series of events that began way back in 1920, I’m not sure this would even be a sport today.

RAY: You’re talking about prohibition! The day they outlawed booze in the United States.

JEFF: I am. Car racing was born when bootleggers souped up their cars so they could outrun the police when they were running illegal booze. Pretty soon, these rum-runners wanted to see just who had the fastest car, and boom. NASCAR was born.

RAY: And here we are watching these folks racing in Vermont.

JEFF: There’s a race I would love to watch involving a legendary rum-runner from Vermont’s past. This woman wouldn’t have raced along a track, though. We’d find her tearing down Vermont’s backroads coming from the Canadian border. This week, we’re exploring the legend of Hilda Stone, the Bootlegger Queen of Vermont.


JEFF: I’m Jeff Belanger.

RAY: And I’m Ray Auger. Welcome to Episode 162 of the New England Legends podcast. If you give us about ten minutes, we’ll give you something strange to talk about today.

JEFF: Thank you for joining us on our mission to chronicle every legend in New England one story at a time. Thank you to the many hundreds of you who have already downloaded our free New England Legends app on your smaht phone. The app connects you to us, plus there’s an interactive map that offers you directions to the location of the stories we’ve covered so far. The map gets new pins each week, but there’s nothing you need to do if you have the app. It updates automatically. Just search for New England Legends in your app store.

RAY: This week’s episode is brought to you by our patreon patrons. Here’s the thing, folks. We want to make New England Legends bigger and better all of the time. With your financial help we can keep bringing you new stories, fancy new things like our app, and more. We believe our content is worth paying for, so if you can help, we’d appreciate your support. Head over to patreon.com/newenglandlegends and sign up for early access to new episodes plus bonus episodes and content that no one else gets to hear. We appreciate all of your support.

JEFF: Ray, since the Covid quarantine so many businesses have been hurt badly.

RAY: Very true.

JEFF: But one business has boomed!

RAY: Yeah! Our friends who run the liquor stores are doing just fine. Can you imagine if the booze supply was shut down these last six months?

JEFF: There would have been even more riots in the streets! But there was a time when the booze supply WAS shut down.

RAY: Right. Prohibition. January 16, 1920… a dark day. The day the 18th amendment to the U.S. Constitution was ratified, which of course banned the transportation and sale of intoxicating liquors. Shutting down entire industries for the sake of temperance.

JEFF: And giving rise to organized crime, homemade booze, and… bootlegging. It was a time when daring law-breakers hopped in their cars, drove to secret locations, and delivered illegal alcohol to the thirsty everywhere. Some of these bootleggers even became pop culture icons.

RAY: Icons, heroes, villains. It can be grey area, can’t it?

JEFF: That it can. So let’s head back to 1925, and meet the Bootlegger Queen of Vermont.


JEFF: It’s the spring of 1925 in Athol, Massachusetts. And Hilda Stone is working as a stenographer. She’s pretty, she wears her hair in a fashionable bob, and has a confident smile.


JEFF: Her husband works in the lumber business, but things aren’t going well for him.

RAY: No, the couple are in financial trouble. It’s getting tough to make ends meet. Hilda’s job doesn’t pay much, and her husband is going broke after the bottom fell out of his business. Desperate, Mr. Stone is determined to find work, but the job search is tough.

JEFF: Hilda, though, isn’t one to wait around. She’s determined to help out anyway she can.

RAY: Hilda also knows a thing or two about illegal booze. She’s paid a visit to the local Speak Easy, and she knows during these roaring twenties, people want to drink, whether it’s legal or not. That’s when Hilda hops in her car…


RAY: And heads north to Canada.


JEFF: Hilda crosses the Canadian border, picks up some cases of beer and bottles of rum and whiskey, then heads back south. The very second she crosses back into the United States… it’s official. She’s now a bootlegger. A rum runner. An outlaw. And Hilda? She loves it!


RAY: With her first trip to Canada under her belt, and wads of cash now lining her pockets from selling the booze, Stone starts thinking about her next score.

JEFF: It doesn’t take too many runs to Canada before Hilda and her husband have enough money to pay their bills again. Considering how lucrative this new line of work is for her, Hilda and Mr. Stone decide to move north to West Halifax, Vermont. And that’s where her operation really takes off.

RAY: As Hilda’s reputation grows, so too does her customer base. There are a lot of people in New England who could use a drink. She’s buying for customers in Vermont, New Hampshire, even as far away as Boston. This enterprise is starting to make her a lot of money. If she’s going to keep up with the growing demand, she’d going to have to increase supply.

JEFF: First, Hilda has her car fixed up.


JEFF: She adds secret compartments to hide the alcohol. She has her engine tuned up so she can drive faster than the police if she needs to. And it’s important to note that there are NOT a lot of women in the bootlegging business. Police and border patrol give women a lot less scrutiny as they cross. She uses that to her advantage.

RAY: Hilda also realizes that driving to and from Canada takes a long time, no matter how fast your engine. And she’s just one person. If she could get more drivers working for her, she could sell even more booze.

JEFF: The next thing you know, Hilda Stone has a gang. And business is booming. The only thing she needs now is a little marketing boost, and that part comes pretty easy. If you need illegal alcohol, you need a bootlegger, obviously. So Hilda dubs herself the Bootlegger Queen of Vermont. And boom, she’s drawing the attention of a lot of new customers.

RAY: Buuuut… when you call yourself the Bootlegger Queen, you’re not only going to draw the attention of new customers….


RAY: Pretty soon law enforcement is also on the lookout.

JEFF: Of course. Their job is to catch bootleggers anyway, so capturing the Queen is bragging rights. Suddenly women crossing the border are drawing more attention because the cops are watching everybody.
RAY: Exactly. And pretty soon, Hilda Stone gets pinched. It’s August of 1925, when border patrol agents nab her for smuggling alcohol from Canada.


RAY: But she’s soon free on bail. After all, her gang has plenty of cash, so paying the bond is no problem. And what does Hilda do while awaiting her trial?


RAY: She makes a run to Canada for more booze.

JEFF: Of course she does. Then comes September.


JEFF: And once again, Hilda is arrested for bootlegging.

RAY: And once again she makes bail. And once again she gets back to work smuggling alcohol.

JEFF: Then comes October.


RAY: You’ve got to be kidding me.

JEFF: Nope. Hilda is arrested again for rum running. Once again she makes bail. Then comes December.


RAY: This is getting downright ridiculous. How many times are the authorities going to let her post bail?

JEFF: This December arrest is a little different, though.

RAY: How so?

JEFF: Police search Hilda’s car and find all kinds of secret compartments that can store dozens of bottles of booze. But, curiously, there’s something authorities DON’T find in the car… there’s no booze. She must have already made her drop off, because there’s nothing illegal in the car, but those compartments are clearly used for smuggling. For their trouble, the police seize the car, and Hilda goes free.

RAY: I’m still shocked someone can get arrested four times in four months for the same crime and still walk free.

JEFF: We need to understand that many police officers don’t like making these arrests. Shoot, some of these cops are probably customers when they’re off duty. There are plenty of otherwise honest citizens who head to Canada for the weekend and sneak home a little booze for themselves on the way back. Police can’t arrest everyone. Plus, alcohol is something that was completely legal just a few years ago. So this isn’t the highest crime in the land. But yes, repeat and flagrant offenders who call themselves Queen of the Bootleggers, must be dealt with, especially when Hilda Stone is getting a lot of ink in the papers.

RAY: By late December, Hilda Stone loses her bail after she refuses to show up in court in Montpelier.

NEWSMAN: The bail of $1500 of Hilda Stone the woman rum-runner, styled the ‘Bootlegger Queen,’ was declared forfeited in the United States court at Montpelier Tuesday by Judge Harland B. Howe, when she failed to appear in answer to a charge of illegal transportation of liquor. The particular offense alleged by the government authorities in this instance was the attempt to smuggle 174 quarts of ale at Canaan, where she was captured.

RAY: And that lands her in jail come February of 1926.


RAY: By now, Hilda Stone has become a bit of a celebrity in the newspapers. And people want to know why Hilda Stone turned to this life of crime. Reporters ask. And she answers.

NEWSMAN: Love for her husband and a mad resolve to help him out of a financial squeeze in his lumber business prompted Mrs. Hilda Stone, of West Halifax, to abandon housework and a life of respectability and turn bootlegger.

JEFF: She did it for love. I love that. Once Hilda finishes her jail sentence in July, she’s reunited with her husband. Now free, and having paid her debt to society, she finds herself staring at her car… (PAUSE) She walks up to her automobile, all souped up, and with all of those secret compartments.


JEFF: She sits behind the wheel, grips the steering wheel. She takes a deep breath.


JEFF: And 23 Skidoo, she’s back in business, baby. Heading north to the Canadian border, because folks are thirsty in New England.

RAY: For the next two years Hilda Stone will get arrested more times, she’ll make her bail, and she’ll skip her days in court. It’s March of 1928, when the law finally catches up with her.

NEWSMAN: Hilda, pretty and young, who has recently narrated the thrills of the game and compared it favorably with the raising of turkeys at her farm home in Halifax, pleaded not guilty to the indictment of smuggling and transporting liquors from Canada into the United States. She is charged with having transported a large quantity of ale, whiskey, vermouth, gin, martini, champagne, and port wine and it is expected will be up for trial by jury here some time tomorrow.

RAY: The evidence is overwhelming. After serving more jail time, Hilda Stone seems to get her fill of rum-running. The Bootlegger Queen of Vermont finally hangs up her crown, and that brings us back to today.


JEFF: Hilda was a bootlegger because she loved the thrill, the freedom, and earning her own money. She became an iconic outlaw who the people of New England loved because she brought them beer and booze. And she made herself quite a bit of money along the way.

RAY: By 1933, Prohibition was repealed, making beer and liquor legal in the United States once more. Bootleggers everywhere lost their lucrative businesses, and many Speak Easies transformed back into legitimate bars. It was the end of an era AND an error.

JEFF: I see what you did there. After 1933, there was still some bootlegging for those items you just couldn’t get in your own state, and some illegal stills continued to operate all over because some folks had the knack for making good moonshine, and there was still the need for fast cars that could run the hooch and evade police. From there, NASCAR was born, and auto racing is obviously still around.


RAY: Yeah, here at Devil’s Bowl, it’s fun to watch these cars whip around the track.

JEFF: Imagine taking one of these cars on one of our infamous beer runs, Ray?

RAY: It’s the car to take when you want your beer NOW.

JEFF: I can’t help but wonder… if Hilda Stone was driving one of these cars right now, I bet she’d give these boys a run for their money.


RAY: One thing that hasn’t changed in the last 100 years is that selling booze is still highly profitable. Especially when we’re stuck inside with not much else to do.

JEFF: Not much else to do but listen to the New England Legends podcast. To post a review for us, and tell a friend about our show! Or maybe even call our legend line at 617-444-9683 and leave our show closing on there for us.

RAY: So true. Also, be sure to check out our Web site. We post pictures with almost every episode. You can even see a picture of Hilda Stone, just click on Episode 162.

JEFF: We’d also like to welcome folks listening to us on Amazon Music’s brand-new podcast service. You can find us on there and subscribe for free, or subscribe to us anywhere you get your podcasts. We’d like to thank Michael Legge for lending his voice acting talents this week, and our theme music is by John Judd.

VOICEMAIL: Hi, this is Debbie from right here in Milford, Mass. Until next time remember the bizarre is closer than you think.

Liked it? Take a second to support New England Legends on Patreon!
Become a patron at Patreon!

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.