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Lyndonville: Once Vermont’s Toughest Town

by Virginia Down

The Boston Evening Transcript headline blared the starling news on July 29, 1931: “Vermont’s Toughest Town Moves to Rid Itself of Gangsters.” Prohibition was at its height with two more years to go before its repeal by the Twenty-First Amendment. The newspaper reported that gangsters lolled on Depot Street, parked their rum running cars in plain sight and sometimes gave local teenagers high speed rides on their back road getaway routes.
The article painted a picture of an apathetic Lyndonville. It calls the village, “The headquarters of one of New England’s biggest bootleg gangs. The authorities of Caledonia County, in which Lyndonville is located thus far have done little, if anything, to rid the community of the dozens of young toughs who have flocked here from western Massachusetts, Rhode Island, and New York to pick up a few dollars in the border rum racket.” The paper complained that the sheriff himself, Frederick A. Flint, refused to say anything to the press worth quoting.
The focus of the article was a heist of contraband liquor which had been hidden in the cellar of the chief of police, H.H. Butterfield, a daytime robbery that stirred townspeople into action. As the newspaper reported, “The boldness of the hijacking alarmed the citizens who had heretofore tolerated the congregation of toughs and wise guys in the boarding houses, the poolrooms, and barber shops, and the lunch counters of the town.”

In 1976, when I was taking a course in oral history at the University of Vermont, Professor Charles Morrissey asked me to consider interviewing an older Lyndonville citizen on those rum running days in Lyndon. My subject was Clayton Fisher, since deceased, who taught science at Lyndon Institute in the 1920s and 30s. He lived in Lyndon Center close to the favorite route of bootleggers who roared ahead of police cars on their race from the Canadian border to Boston.
“There wasn’t any strong reaction to Prohibition in town for the simple reason that Lyndonville was a dry town,” Fisher explained.
Lyndonville had always had prohibition.” Once the bootleggers discovered the ease of cruising through the sleepy little village, the action began.

Downtown Lyndonville during the Prohibition era Photo on left: Downtown Lyndonville during the Prohibition era

“The traffic came through the Center and close to our home, which abutted the main road, and they went roaring down through there a good many nights,” Mr. Fisher recalled. “They’d pile as much liquor as possible in these Model 62 Cadillacs and they’d do more than 80. We could hear the cars coming a half a mile up the other end of the village. A 61 Cadillac had a gear that whined at high seed. Well, they couldn’t do that safely down our road because there was a water bar right in front of our house. One rumrunner’s car took off on that bar, went some fifteen feet through the air and broke a wheel when it came down. “He paused in reflection, then added, “That load was well distributed beside the road and around the neighborhood!”
“I dressed hastily and got up just too late to see the car smashed up. The broken down car and officers’ cars following it were within a couple hundred feet of the house. They were carrying Canadian ale in gunny sacks piled high in the back seat of the Cadillac. Such wrecks and captures were fairly common.” Lyndonville was spared the high-speed chases. It served as a meeting place for bootleggers. “They had it all fixed somehow,” Mr. Fisher explained. “Occasionally, truck loads of contraband liquor were parked along the main street in Lyndonville. Law enforcement was poor. It was said that the rum running was managed by a couple brothers in Lyndonville and they behaved themselves, employed sober drivers and mechanics.”
Some of Lyndonville’s businesses thrived on bootleggers’ needs, he recalled. “They patronized the local garage for maintenance of automobiles, which was heavy for cars used like that. Also, the drivers and mechanics hired rooms. They brought money into the community and at first many Lyndonville people didn’t want anything done about it.
But, as The Boston Transcript story revealed, things eventually got out of hand around 1928. “There were all kinds of rowdyism, drinking parties and noise on the streets at night, and a policeman was assaulted and seriously injured,” the article declared. “So people began to see it was not a harmless diversion. Still, law enforcement agents did very little about it and there were various reports that the county sheriff was involved with the rum business in a corrupt manner.”
Mr. Fisher said that it was common for cars that had been sized to be sold at auction. The same rumrunners would buy them back. “One particular Cadillac was sized and put back on the road four times in two years.” Smuggling by passenger train was a regular occurrence, he continued. “Passengers used all kinds of schemes. One was to hang the bottle on a cord outside the widow before the officers came through. Some local youngsters got wise to that and went along and picked off the bottles, in an interesting kind of a double cross.”
When Herb Gallagher of East Burke was a high school student at Lyndon Institute, he and his friends arrived upon the scene of a dumped load of illegal beer. “It was a summer day when we were swimming in Vail’s Pond. One of the kids came along and said, “there’s a whole load of beer down over the bank near Mr. Mathewson’s house.’ Everybody grabbed their shoes and ran. Even little kids were dragging cases of beer off into the bushes. I hid two cases in the brook and made a little waterfall so it would go over and out.” He chuckled as he recalled the ingenuity of one boy. “Charlie Breason had a little handcart. He put two cases on the cart, threw a coat over it, and went right up through Lyndonville. I didn’t drink beer then but you could sell it for one dollar a bottle.”
Pilot cars often accompanied the speeding Cadillacs and laid down smoke screens to outwit pursing cars. Herb was once the victim of such a smoke screen while driving north to Island Pond with a friend on a fishing trip. “Just as we came out of a wooded area there was a car going in the opposite direction and the driver touched the thing off. I always suspected he mistook me for the law. You couldn’t drive through it. You had to stop.”
He recalled seeing the Cadillacs around town. “They had reinforced springs in them and when they were driving around town empty, the hind end would stick right up in the air. They looked like they were going downhill.”
Herb describes an unplanned nighttime adventure when he and a high school pal, Hugh Vavis, were walking with dates across the park in Lyndonville toward the path going to the old ball field. Two other boys, Walter MacDowell and Carl Dahlbeck, decided to surprise them into the ball field and shine a flashlight on them. But the scheme didn’t work. Herb explained why they changed their route. “We heard a lot of commotion and clanking of bottles coming from down there, so we decided we weren’t going. But I guess we missed all the fun.” Later Herb discovered the other boys had flashed the light on two bootleggers drinking hijacked beer in their truck. The men gave chase and the boys had to run for safety across the river on a swing bridge. One rumrunner fell off the bridge and had to be retrieved by his partner. Clayton Fisher’s theory about who financed the Lyndonville rum running operations was based on persistent rumors in town at the time. “It was widely circulated that it was financed by Milk Street bankers, and that a considerable amount of the hard liquor went to hospitals in Boston. It was believed that crooked doctors, none of them from Lyndonville, made more money with those ‘prescriptions” than with their medical practice at the time.”
He summed up Prohibition as “a disastrous social experiment. It diminished respect for the law. Juries wouldn’t convict and unenforceable laws are better off the books.” Prohibition ended in 1933 and the town of Lyndon settled back into its quiet, untroubled existence. The years of smuggled goods and bootleggers’ chases gradually faded from memory.The previous piece of work was first published in 1991 in a book titled, “Mansions & Meadows: Lyndon the Way it Was.” Downs wrote the book in honor of Lyndonville’s bicentennial.