Winchester center, among other places around town, was the scene of many arrests for violations of the Prohibition liquor laws which were in effect from 1920 to 1933.

WINCHESTER – A century ago, Winchester, along with the rest of the country, entered Prohibition.

Intended to improve health, morals, safety, and domestic conditions, the 18th Amendment banned the production, importation, transportation, and sale of alcoholic beverages. But the reform so failed that it was repealed in 1933.

Winchester was already a dry town, granting no licenses to sell liquor. It had temperance societies which celebrated on Jan. 16, 1920, when the Amendment took effect. Nevertheless, as news reports reveal, the town was not dry in practice.

When the July 4th celebration came along in 1920, The Winchester Star reported, “Some misguided ones took the date as the opening event in the home brew competition, and those who got by are still undecided whether they were more fortunate with their head aches that those who found a haven of refuge within the arms of the Law. We in Winchester appear to still have with us a little of the 1918 stock.”

Residents not only stocked up before Prohibition began, they also managed to replenish their supplies. For example, in 1926 the attention of two policemen was drawn to two men in a touring car who made several stops at west-side homes where they delivered neat bundles. After about a half-hour’s observation, the officers decided to investigate.

When accosted on Everett Avenue, the men attempted to escape but were caught after a chase. The car was found to contain “six bundles of choice ‘assorted’ liquors, evidently assignments for immediate delivery,” the Star reported. The judge found the men guilty of keeping and exposing with intent to sell and fined each $75.


Whether residents wanted liquor or not, “Chief McIntosh and his faithful minions of law and order will allow no illicit distillers and purveyors of ‘hootch’ in Winchester,” the Star declared in 1922.

Prohibition introduced new criminal offenses. McIntosh and his men conducted several raids annually, arresting residents for the illegal sale of alcohol. The first reported raid was on June 3, 1921, when police found a still and three gallons of alcohol at a house on Summer Street.

A more impressive haul was made that September. Police suspected some illegal goings-on at a house on Cross Street due to the odor of alcohol in the neighborhood and mysterious visits to the house. The chief and four officers paid it a visit. Though the resident initially expressed wonder at their presence, their finding a 30-gallon copper still, along with about 40 gallons of moonshine, led to his arrest and a court-imposed fine of $50.

Over the years other residents were caught making and selling liquor as raids were carried out on Swanton Street, Kendall Street, Spruce Street, Sylvester Avenue, and elsewhere. Those arrested were generally fined and/or sentenced to a few months in jail. Some then went right back into business.

One of these raids should have been a warning against buying home brews. In December 1924, police seized 88 quart bottles and a half-full keg of beer in a raid on Harvard Street. The “hootch” was stacked on the piazza.

While Officer John Hogan was carrying a case of nine bottles to the police car, the bottles burst without warning, showering Hogan with broken glass and fizzing beer. The force of the explosion caused him to lose his balance and fall down the stairs.

Hogan’s face and head were badly cut and he reportedly narrowly avoided losing his eye-sight. He also had a sprained wrist and gashed leg from the fall. He arrived at the doctor’s office with a face covered in blood and a uniform covered in frozen foam.

Sensational raid

On occasion it was out-of-towners to blame for the liquor nuisances in town.

At the end of July in 1923, Chief McIntosh’s suspicions were aroused by activities at an isolated estate, including a cranberry meadow, in back of the river at Washington Street near the Woburn line.

McIntosh noted new movements at the old cranberry house and the repair of the old driveway. On a day when smoke was issuing from the chimney, he collected four officers, and they arrived just as a truck was about to drive away with 75 gallons of alcohol. With revolvers drawn, police kept the men inside the shed from escaping.

The current occupier of the house told police that the bootleggers, residents of Chelsea and Winthrop, rented the place for a garage. But they turned it into a plant for redistilling an alcohol rub into pure alcohol. Inside the shed, police found more than 500 gallons, along with a 400-gallon copper still, all valued at more than $4,500.

Hundreds of people gathered as the police completed their raid, and the Star later reported that the police needed two one-ton trucks and one five-ton truck to deliver the stuff to the state authorities.


Another nuisance police had to deal with was motorists transporting alcohol through the town. Many doubtless got away with it, but others gave themselves away by accident, a traffic offense, or simply a dumb mistake.

In May 1924, an automobile stalled on the center railroad crossing. A train being due soon, an officer and bystanders pushed it off. While the driver attempted ineffectually to get the car to go, two officers lifted the side curtains and saw several burlap bags. Their noses told them what they contained. The car was loaded with five-gallon cans of alcohol.

In August of 1924, Officer John Regan was in the center when he stopped a truck driven by two men whose actions seemed suspicious. Though labeled “Gordon’s Ginger Ale,” the contents turned out to be 75 cases filled with beer.

Two weeks later, Winchester police made one of the biggest liquor hauls outside of Boston – 2,000 gallons. While Sgt. William Rogers was watching for speeding vehicles at the junction of Main and Washington streets, he saw a five-ton truck approaching in what he deemed an unsafe manner and stopped it. His conversation with the driver, a Charlestown man, raised his suspicions. His examination confirmed them; the truck held about 200 boxes filled with cans of Belgian alcohol.

The truck, the Star reported, “proved an object of curiosity to habitués of the center until removed by the police to a place of safe keeping.” The driver was fined $150.

On the afternoon of Sept. 23, 1925, after the town had installed new stop-and-go traffic beacons at the intersection of Mt. Vernon and Main streets, Sgt. Thomas Cassidy noticed a Ford touring car disregard the signal. Hastening to enlighten the driver, Cassidy found him to be very nervous. The car was completely closed in with side curtains, and the tonneau was covered with blankets, all hiding 5-gallon cans of liquor.

In 1927, a bootlegger in a Cadillac stopped on Oxford Street to ask Patrolman WiIliam Cassidy for directions to a nearby house. According to the Globe, seeing the man mistake the house, Cassidy went after him to correct him. According to the Star, Cassidy later saw the same car parked in a private garage and went to examine it. Either way, the bootlegger took flight. Cassidy caught him and discovered 81 bottles of liquor in his car. The judge imposed a $200 fine.


The money to be made in the liquor trade was a temptation, even to those supposedly fighting it. One story covered step by step in the Boston Globe told of a conspiracy among an infamous bootlegger and members of the Coast Guard, including the former executive officer of Base 5 at the East Boston Base, a Winchester resident.

The Coast Guard operated a Rum Patrol to deal with the smuggling of liquor into the country. Although rumrunners generally had the fastest boats in the water, it also helped if they could bribe Coast Guard men into cooperating.

In 1928, five members of the Coast Guard were among 11 men who went on trial on a charge of conspiracy to smuggle liquor. The jury was hung on the case of the Winchester man, and the judge declared a mistrial. As the investigators gathered additional evidence for a new trial, he changed his plea to guilty and was sentenced to an undisclosed jail term.

The Star tactfully kept quiet on the matter and allowed the man’s younger son, a popular all-round high school athlete, to be the local news maker. The family left town a little over a year after the case ended.


By far the most decried liquor problem during Prohibition was drunk drivers. An average of 24 arrests were made yearly in Winchester, generally following an accident. Fines ranged from $50 to $100. However, this was not a problem solved by the repeal of the 18th Amendment nor, in fact, by any means yet known.

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