Prohibition in Vermont started early. Liquor officially became illegal in parts of Vermont in the early 1800s, with towns demanding the right to outlaw sales of alcohol within their borders. In 1850 the state officially banned licensing alcohol-selling establishments and two years later banned all manufacturing of alcohol. With that, the state went dry – sort of.
Enforcement of prohibition was always a spotty affair, with each town and county taking its own approach to policing liquor sales. In some places, alcohol virtually went underground. But others openly tolerated saloons, though the growing temperance movement in the country began pressuring Vermont cities and towns to crack down on the “rum holes” in their midst.
Vermont’s remote northern border was always popular with bootleggers. Bringing liquor surreptitiously from Canada to avoid taxes was a common enough activity. But with the change in the laws in 1850, it became far more attractive. The crackdown on domestically produced liquor pushed the demand for bootleg hooch through the roof. The border region became a hotbed for bootlegging right through the era of nationwide prohibition in the 1920s.
Catherine Dillon Comes to America
Into this turbulent environment came Catherine Dillon. If you were given just two words to describe Catherine, you wouldn’t go far wrong with “beautiful” and “feisty.” She came to America in 1851 to Oswego, N.Y. at roughly the age of 25. Catherine (maiden name Driscoll) was part of the wave of Irish immigrants who poured into America. Famine, political persecution and economic recession in Ireland made America look like a paradise of jobs and opportunity.
In northern Vermont and New York, the railroads provided jobs for the Irish. Catherine Dillon, meanwhile, decided to provide them with everything else — food, shelter and drink.
Following the workers as they migrated from railroad to industrial jobs, Catherine moved from Oswego to Rouses Point and finally across into Vermont, spending time in Swanton and finally settling in St. Albans. There she and her husband, Patrick, began assembling a small village of tenements populated with her fellow Irish immigrants. In addition, she offered alcohol at two saloons, and it didn’t take long for the law to notice.
In December of 1854, in Franklin County Courts, Catherine and Patrick were fined $40 for illegally selling liquor. Patrick went to jail for failing to pay the fine. And in December of 1855, Catherine was back in court, this time sentenced to three months in prison.
Courts and Jails
Catherine fought the charges with a vengeance all the way, at one point losing her case only because her lawyer didn’t get an appeal filed fast enough.
In March of 1856, the police found six barrels of liquor on her property during a raid. No one was willing to step forward and admit they owned the booze, and so it was ordered dumped.
Around 1857 she sought a divorce from Peter. She claimed he was abusive. Peter argued that anyone who knew Catherine knew he was no match for her. The story of how she finally rid herself of Patrick goes like this: One day they arrived back in Vermont on a train and Patrick went to collect their luggage. Catherine pointed out a suitcase and told him to take it. It didn’t belong to her, however, and she reported her husband to the police and had him jailed. The incident was enough to send Patrick packing, off to the Army as a bugler. How much of the story is true and how much is legend remains a mystery, but it was reported in her obituary.
Meanwhile, Catherine’s legend grew. In one instance, a man died after getting drunk in her saloon. She initially faced manslaughter charges, but they were dropped. In other cases, she would be arrested, only to escape and be back in business within days. The ease with which she navigated the legal system left many wondering if she wasn’t managing to corrupt the police.
Prohibition in Vermont Gathers Steam
By 1865 the calls for putting a stop to liquor sales were growing louder. In 1868 Catherine was convicted of smuggling liquor from Canada and fined $1,500. She disappeared, leaving the sheriff to seize her animals and property to settle the fine. In another case, two men claimed she waved a pistol at them when they approached her about paying a bill.
While prohibition in Vermont still had a long run ahead, Catherine Dillon did not. Finally the persistent fines and costs of fighting in court got to Catherine, and she gave up the liquor trade around 1870. Whether she would have stayed out of the business is a moot point. In September of 1871 Catherine suffered $5,000 in losses when a fire swept through St. Albans and destroyed a large section of the city.
By this point Catherine was nearing the end of her life. At just 45 years of age, she died alone in her house. She left a considerable estate, including 125 acres of land, a farm, tenement houses and commercial buildings. Estimates put its value at somewhere between $50,000 and $75,000.
Catherine’s two brothers were the beneficiaries of her estate, though her death would eventually provoke a protracted lawsuit. A long-lost sister argued she was owed a portion of the estate. She charged that her brothers, though they knew how to find her, neglected to tell her that Catherine had died a very wealthy woman.
This story was updated in 2023.