Hilda L. Stone (née Green; born August 1897) was an American bootlegger who smuggled liquor from the Canadian border to Boston during the Prohibition era. Operating from her home in West Halifax, Vermont, she transported premium liquors through New England to serve elite clientele in the Boston area. Active between 1925 and 1928, she was known as the "Queen of the Bootleggers" and "Duchess of Alcohol." She was arrested multiple times for smuggling violations and was sentenced to six months imprisonment in January 1926. Stone later became a federal fugitive after failing to appear for new charges in 1928.
Early life Hilda L. Stone (née Green) was born in August 1897 in Taftsville, Vermont. She was 28 years old at the time of her imprisonment in February 1926, though border patrol rumors circulated claiming she was between 30 and 45 years old. Stone's father was born in Connecticut and her mother was from England. She had two sisters and one brother. Stone's parents were described as "good, honest, everyday" people who were respected in their community.
Stone attended village school in Taftsville and graduated from Randolph High School in Randolph, Vermont. She subsequently completed a course in bookkeeping and stenography at a business college in Burlington, Vermont.
Stone described her early life as that of "the average girl in a rural New England community," noting she was "a sort of tomboy" who loved outdoor activities including fishing and hunting. Her father taught her to use firearms from childhood, and she became "a pretty good shot," though she deliberately chose not to carry a revolver during her smuggling operations, stating it was "apt to get you in bad."
Stone was raised with strong religious influences, attending Sabbath School and church regularly both before and after her marriage. She described herself as "studious and judicious as a girl" and maintained a good reputation in her community until she began bootlegging.
Stone described herself as "old-fashioned," preferring traditional waltzes to the Charleston dance craze, though she enjoyed jazz music. She did not smoke or drink alcohol, later stating she "loathed" alcohol and never smoked cigarettes for health reasons. Despite her traditional personal habits, Stone held progressive views on gender equality, stating she didn't "believe in a double moral standard" and that "women have as much right to drink and smoke as men have, if they care to."
After completing business college, Stone's parents moved to Athol, Massachusetts, where she worked as both a bookkeeper and stenographer.
Stone married Frank Stone when he hired her mother to do bookkeeping work for his lumber business. Stone took over the work as a "confidential secretary," conducting evening bookkeeping sessions in her parents' dining room. During these sessions, Frank courted her with candy, flowers, and invitations to the theater. He eventually proposed during one of their business meetings, and Stone recalled being "unutterably happy" when she accepted. They were married by the Rev. Mr. Peak on July 30, 1917 in Athol, Massachusetts.
After marriage, the couple moved to West Halifax, Vermont, where Frank operated his first sawmill, and he later established a second mill in Harrisville. Stone continued managing Frank's business affairs, keeping track of his books, collecting letters and bills, and spending considerable time traveling by automobile for business purposes, experience that later proved valuable for her bootlegging operations. The couple had no children.
Stone claimed West Halifax, Vermont as her home, though law enforcement sources indicated she came from Colrain, Massachusetts. The two towns are adjacent along the Vermont-Massachusetts border, and the family's property may have straddled both jurisdictions.
Contemporary newspapers referred to Stone by various nicknames including "Duchess of Alcohol," "Bobbed Bootlegger," and "Queen of the Rum Runners."
Bootlegging career
Operations As her husband's lumber business faced financial difficulties and potential bankruptcy, Stone abandoned housework and began bootlegging operations to help with the financial crisis. In her autobiographical account, Stone described Frank's lumber business as having suffered serious financial setbacks in the year before their marriage. Stone stated that she made the decision to enter rum-running in June 1925 at her home in West Halifax, after spending months seeking ways to save the business from ruin. Stone made her first smuggling trip on May 11, 1925, when she traveled to the Canadian border with her guide Tony to purchase ale. In a jail interview, Stone described her turn to rum-running as motivated by "love for her husband and a mad resolve to help him out of a financial squeeze."
Stone served as a principal field agent in a Massachusetts-based rum-running operation, transporting liquor from the Canadian border through New England to Boston. For her first smuggling trip to the Canadian border, Stone was guided by an associate she identified as "Tony," who introduced her to the smuggling network and taught her the routes and methods. Stone also worked with another guide known as "Pete the Prowler," who was familiar with all the rum-running roads.
Stone's first customer was a prosperous, middle-aged Boston businessman who placed an order for 30 cases of premium liquors, including Veuve Clicquot, Mumm, Pol Roger, and Pommery champagnes, along with Scotch whisky and cognac. The size of this initial order convinced Stone she needed a larger vehicle than her roadster. Her second trip to the Canadian border was her first solo delivery, marking her quick progression to independent operations.
As her business grew, Stone upgraded from her roadster to a larger used coach, which she purchased with cash to avoid installment obligations. She had the vehicle tuned "like a racing machine" and kept her roadster as a backup. Stone had a false bottom professionally installed on her coach by a specialist recommended by Tony, and also equipped the vehicle with curtains and blankets to conceal loads during transport.
When she needed to purchase this larger vehicle, Tony introduced her to Harry Murdock, a 200-pound mechanic who would inspect the vehicle. Murdock was both a skilled mechanic and expert driver, and Stone hired him as her chauffeur after witnessing his abilities. Stone systematically tested Murdock's capabilities as a bootlegger by taking him on one of her established routes. Despite her own eight years of driving experience, Stone was impressed by Murdock's superior skills, noting he could "burn up the road without taxing the car," and described him as "level-headed and big and plucky enough to be a real protector in an emergency."
Murdock's exceptional driving skills helped them escape from dangerous situations, though Stone noted they were "nearly killed several times in desperate attempts." Murdock advised Stone on vehicle maintenance, emphasizing the importance of quality tires and spare equipment for high-speed police pursuits, noting that a tire blowout during a chase with armed police could be catastrophic.
Despite strong warnings from Tony and Murdock, who told her that solo border runs required "the iciest kind of man's nerve" and was not "a woman's job," Stone insisted on making solo trips to prove her capabilities, declaring "I am going through alone or bust."
Stone and her associates paid Pete the Prowler for intelligence about patrol schedules at the border, allowing them to time their crossings when enforcement was minimal. The Prowler also actively assisted during smuggling runs, riding ahead on his motorcycle to scout for patrols and using hand signals to warn Stone of danger, pointing with his left arm to indicate locations and winking to signal when it was safe to proceed.
Stone described operating "on a business basis" within the smuggling network, where associates treated her with professional respect due to her serious approach to the work and her status as a married woman supporting her husband's business.
Stone contrasted her professional approach with that of reckless operators in the smuggling network. She noted that "girl blinds"—female companions used by male bootleggers for cover—often proved to be security risks due to their tendency to gossip and engage in "riotous living." Stone avoided this lifestyle, maintaining a quiet profile and resting between trips. She also observed that another bootlegger, Jimmy Hayes, despite being clever, would drink and boast about his exploits in public places, behavior she considered "the height of folly."
Stone modified her vehicle for bootlegging, installing improved suspension and a high-powered engine to evade law enforcement. The car also featured a secret compartment for concealing liquor and carried license plates from multiple states. Stone avoided detection by studying maps, varying her routes, and rarely returning by the same path she took outbound, attributing her success to both luck and systematic planning. During her smuggling runs between Canada and Boston, Stone stopped at establishments including the Four Poster Inn in Burlington and Whitehall.
When confronted by border patrols, Stone posed as a lost American tourist, telling officers "I'm lost in a strange country" and playing a demure, innocent role. She carefully controlled her speed during border crossings, initially driving at 35 miles per hour before deliberately slowing to 20 mph to appear like a cautious tourist. Stone concealed liquor under both seats and piled under blankets in the back of her vehicle, with a suitcase placed carelessly on top to create an appearance of normalcy.
On one notable trip, Stone successfully evaded Canadian border patrols twice—once while entering Canada when the Prowler warned her to hide her contraband before a patrol arrived, and again on the return journey when she used careful speed control and deception to pass through a patrol checkpoint. During the return crossing, a patrol officer who had unknowingly directed her to a liquor supplier earlier vouched for her to another officer, calling her a "Yankee flapper who lost her way," allowing her to pass through with a full load of contraband.
In interviews given while incarcerated in Washington County jail, Vermont, Stone described herself as an expert motorist and marksman who had been familiar with firearms since childhood. She conducted many of her deliveries in broad daylight, parking her liquor-laden automobile on Massachusetts Avenue in Boston, between Boylston Street and Commonwealth Avenue, where she would wait for buyers to arrive and signal for delivery to suburban mansions. Despite police officers passing by during the midday rush, her activities went undetected.
Stone claimed to supply liquor to prominent Boston-area customers, including society men and women, millionaires, business and professional leaders, and public officials, many of whom she said were listed in the Social Register. She worked through a Boston agent whose identity she declined to reveal, stating that disclosure would "be a sensation in itself, because of his prominence in business circles."
Stone's Boston distributor, whom she referred to as "Mr. Blank," gradually revealed the identities of his customers over several weeks as he built trust with her. The clientele included a major manufacturer and a state official, with deliveries made to "splendid estates." Stone specifically described her customer base as including "blue bloods and millionaires," business and professional men, public officials, and society women, whom she referred to as "women tipplers." She stated that she supplied "some of the most notable families in Greater Boston" and "well-known public officials," but refused to reveal their identities, saying their names and addresses would cause a sensation.