On Dec. 5, the U.S. will celebrate 93 years since the ratification of the 21st Amendment and subsequent closure of alcohol prohibition in the United States.
The failed, 14-year experiment known as prohibition brought an array of larger-than-life gangsters, smugglers and rum-runners into the limelight in Franklin County, providing the jazz era with the one thing it was missing: booze. Chicago had Al Capone, Memphis had Machine Gun Kelly and Franklin County had Hilda Stone, the “Queen of the Bootleggers.”
A Colrain housewife, booze smuggler and lieutenant of a rum-running crew in Greenfield, Stone was quoted in Recorder archives as saying she smuggled liquor for the “thrill” of evading law enforcement.

According to Historical Commission member Sarah Bolduc, the invention and mass production of the car made running illegal liquor from Canada back into the U.S. a largely profitable business, with women emerging as a key demographic in the 1920s.
“Women were actually said to be incredibly good at rum-running. In fact, there was an estimated five-to-one sales difference between women and men, because part of it was the fashion of the era. You know, everyone’s kind of heard of women smuggling bottles in their long fur coats,” Bolduc said. “Once they could drive a car, they got a level of independence that really hadn’t been seen before … Women like Hilda Stone, who was a housewife from Colrain and was, by all accounts, just an average person, was suddenly able to have this large amount of freedom that was able to help her.”
Archived accounts of Stone’s backstory suggest that she was married to a lumber mill owner in Halifax, Vermont. As the family approached bankruptcy, Bolduc explained that Stone reportedly decided to “abandon housework” and turn to a life of crime. The problem, Bolduc explained, was that she was “too good” at bootlegging.
Between 1925 and 1928, newspapers from across the country had written about Stone’s arrests in the illicit booze trade. One of the earliest publicized reports of her arrest was a story published in the Aug. 21, 1925 edition of The Recorder, detailing the moment Stone and a man named Harry Murdoch were arrested at the Vermont Border after attempting to smuggle liquor. Stone refused to go down without a fight.

“Officers said the man and girl leaped from their machine when overtaken and that the girl drew a revolver, but made no attempt to fire upon them,” The Recorder wrote in 1925. “They were arraigned later and held in $500.”
Stone’s criminal talent continued to make headlines, and by Dec. 22, 1925, The Recorder had printed her name again, this time not referring to her as “the girl,” but as the “Bootlegger Queen,” who had skipped out on bail after having been arrested for the “fourth time in recent months.”
Only a month after her August, 1925 arrest, Recorder reporters wrote that Stone had been arrested and released from jail in a “misunderstanding” in northern Vermont and was once again arrested that autumn when she was caught driving in a car filled with “whiskey, ale, vermouth, gin, champagne, cognac and wines.”
Between August and December of 1925, Stone had also been arrested after she was caught driving north with a man from Providence, Rhode Island in a car containing a secret compartment and license plates from four different states.
That same Dec. 22, 1925 Recorder article also identified Stone as one of the “principle field agents” of a Massachusetts “rum ring.”
“She has admitted a fondness for the ‘thrill’ of pursuit by customs officers, but admitted also that she raises turkeys when business is dull,” The Recorder wrote in December 1925.
“Not only was she good at rum-running, but apparently, after a while, it stopped being about the money for [Stone], and she told authorities that she likes to run liquor for the thrill of it,” Bolduc said. “What probably started as taking the family car and going all the way up to Canada, soon became a hardcore operation. She also had a modified car. She got better shocks and she had a high-powered engine installed.”

In a February 1926 profile on Stone, published by the Yonkers Herald, she described herself as an “expert motorist” and a “crack-shot” marksman, who had been familiar with firearms since childhood. Stone, described by the newspaper as being “young, refined, educated and pretty,” was reported to have made her transition into the smuggling business as a means to save her husband from bankruptcy.
Stone, in The Yonkers Herald, outlined the distribution of liquor from the Canadian border, through New England down to Boston, where everyone from speakeasy patrons to “public officials” and “millionaires” enjoyed the flow of booze she provided.
Stone told the newspaper that most of her liquor sales and drop-offs were conducted in broad daylight on Boylston Street in Boston, where surrounding officers did not detect the crimes in plain sight among the busy flow of traffic.
Local authorities, Bolduc explained, often turned a blind eye to bootlegging during the prohibition era โ a statement best fortified by the Law Enforcement League of Greenfield, the chair of which, Geo. W Cary, said he was shocked that the Greenfield Police Department stated they knew very little about Stone, The Recorder reported in December 1925.


“The claim of the police department that it knows very little about Hilda Stone, rum runner captured in northern Vermont, surprises the Law Enforcement League, whose members have known about the activities of this woman for a long time,” The League wrote in a statement released by the Recorder. “We have no legal evidence of her making liquor deliveries in town, as we are not collecting it at present, but … there is not but the slightest doubt that Mrs. Stone has done a very large business in this vicinity.”
Further coverage of Stone reports that locals in Greenfield, including former Greenfield Police Chief Thomas Manning, knew nothing of the infamous bootlegger, a claim that Bolduc said was not uncommon during the prohibition era.
“The fact that she was toted around publicly as this hot-headed woman who was just blasting through the back roads of Vermont … the fact remains that she was obviously, at the time, receiving high profile attention from articles like the New York Times,” Bolduc said. “I would dare to say that it was probably the attitude of ‘No, we have no idea who she is, just ignore the silver flask behind my desk.'”
While Stone’s fate remains a mystery, as attempts to find newspaper clippings detailing her death have been unsuccessful, stories found about Hilda Stone are not unique in the prohibition era.
On a week-by-week basis, articles detailing illegal liquor busts filled the pages of newspapers like the Recorder, ranging from one account of a secret wine stash room found within a Deerfield home, to cider- and rum-making operations being raided throughout rural Massachusetts and Vermont. While booze seizures may sound strange to the modern ear, Bolduc said that the tale feels slightly familiar given the modern war on drugs.
“Prohibition, I think, is an excellent example of what it was like in the 20s, and as we go into the the new 30s, I always think it’s incredible to reflect on the past and all the things that have changed, but especially what stayed the same,” Bolduc said. “You can find stories right now of people who wear night vision goggles and drive down the back roads in Maine, surprising and running off the cops, running drugs. It’s just so funny, the phrase just kind of holds true; the more things change, the more they stay the same.”
