Speakeasy in Boston – From Scofflaw to Kennedys

Boston – a Puritan city that drank more than ever

Boston is a city of paradoxes. Founded by Puritans who fled England in search of religious freedom – only to prohibit most pleasures. The cradle of revolution, where colonists threw tea into the harbor because they did not want to pay unfair taxes. And finally – one of the most "wet" cities in America during Prohibition, where illegal establishments were four times more than legal bars before the ban.

Before the 18th Amendment, Boston had about one thousand licensed bars. At the peak of Prohibition, there were an estimated 4,000 speakeasies operating here. Four of them operated on the same block as the police station. This was no accident – it was Boston's version of protest.

In this city, the word "scofflaw" was born – invented to shame drinkers, but proudly adopted by them. Here, a molasses flood killed 21 people because a factory rushed to produce rum before the ban took effect. Here, Irish gangsters controlled the waterfront, Harvard students drank heavily, and Joseph P. Kennedy built a fortune, the sources of which are still disputed today.

Here is the story of Boston during Prohibition – a city that had no intention of listening.

4,000 speakeasies – a fourfold increase

When Prohibition went into effect on January 17, 1920, Boston already had a long tradition of drinking. Irish immigrants, who made up the largest ethnic group in the city, treated the pub as the center of social life – a place where politics were discussed, business was conducted, and everything from christenings to funerals was celebrated. The ban on alcohol was not so much a legal issue for them as a cultural attack.

The reaction was immediate and massive. Within months of Prohibition taking effect, illegal establishments began to spring up – in the basements of tenement buildings, behind restaurant backrooms, in attics, and in private homes. By the mid-1920s, the estimated number of speakeasies in Boston and its surroundings reached 4,000 – with one thousand legal bars operating before the ban, this meant a fourfold increase in places where one could buy a drink.

The police that did not want to enforce the law

The Boston police found themselves in an awkward position. Most officers were of Irish descent themselves and did not particularly care about the ban, which they considered absurd. Federal agents regularly complained that the local police were sabotaging raids – warning speakeasy owners of planned actions or simply "not noticing" establishments operating right under their noses.

The most telling example? Four speakeasies operating on the same block as the police station in downtown Boston. Officers walked past them every day on their way to and from work. No one reacted. Several police officers were even convicted of running their own illegal establishments – which did not particularly surprise anyone in Boston.

Massachusetts says "no"

It is worth noting that Massachusetts was one of only two states (along with Rhode Island) that voted against the 18th Amendment to the Constitution that introduced Prohibition. The state that initiated the American Revolution consistently opposed the ban imposed from Washington. For Bostonians, Prohibition was another instance of "taxation without representation" – a law imposed against their will.

“Scofflaw” – a word meant to shame that became a badge of pride

In 1924, wealthy Bostonian Delcevare King came up with an idea that was supposed to save Prohibition. He proposed a public contest for a new word – one that would shame people breaking the alcohol ban. He announced a prize of $200 (equivalent to over $3,600 today) for the best neologism.

The contest generated enormous interest. 25,000 entries were submitted from across the country. The winning word was “scofflaw” – a combination of “scoff” (to mock) and “law” (law). Two participants independently proposed the identical word: Henry Irving Dale and Kate L. Butler. They shared the prize.

When shaming becomes pride

What happened next is perhaps the best evidence of how spectacularly Prohibition was losing the battle for the hearts and minds of Americans. The word “scofflaw” – invented as an insult – was immediately adopted as a badge of honor by those who drank alcohol.

Within two weeks of the contest results announcement, bartenders at the legendary Harry's New York Bar in Paris (one of the favorite spots for American expatriates) created the “Scofflaw Cocktail” – a mix of rye whiskey, dry vermouth, lemon juice, grenadine, and a dash of orange bitters. The drink became an instant hit among Americans in Europe, who proudly ordered a drink named in honor of their defiance.

King's contest turned out to be one of the biggest public relations failures of the Prohibition movement. Instead of creating a stigma, it created an identity. Instead of shame – solidarity. The word “scofflaw” has permanently entered the English language and is still used today – but not as an insult. It simply means someone who disregards the law, often with a hint of admiration.

The Great Molasses Flood – a disaster caused by Prohibition

On January 15, 1919 – the day before the ratification of the 18th Amendment – one of the most bizarre disasters in American history occurred in Boston's North End.

A huge molasses tank belonging to the Purity Distilling Company at 529 Commercial Street burst without warning. 8,700,000 liters (2.3 million gallons) of thick, dark brown molasses poured into the streets of North End at a speed of 56 km/h. The wave reached heights of up to 7.6 meters.

Why the tank burst

Purity Distilling Company was desperately rushing to process as much molasses into industrial rum as possible before Prohibition closed the door to profits. The company filled the tank beyond its capacity, ignoring visible warning signs – the tank leaked so regularly that neighborhood children collected the molasses seeping from the cracks.

Investigations after the disaster revealed that the tank was poorly designed and had never undergone a pressure test. The company painted it brown to make leaks less visible. The rupture occurred during a sudden warming – the temperature rose from -17°C to +5°C within a few hours, causing the molasses to ferment and increasing the pressure inside the tank.

21 fatalities

The wave of molasses destroyed everything in its path. 21 people died, 150 were injured. Among the victims were workers, children, and passersby. Several horses got stuck in the molasses and drowned. The steel structure of a nearby railway viaduct was bent by the force of the impact.

The rescue operation lasted for days. Rescuers struggled to move in the thick, sticky substance. Molasses reached the harbor, turning the waters brown. Cleaning the entire neighborhood took several months – 300 people scrubbed the streets with sand and salt water for weeks.

Residents of North End claimed for decades that on hot days, the smell of molasses could still be felt. Historians consider this more of an urban legend, but the fact that the substance soaked into wooden buildings and cobblestones is documented.

In 2019, on the 100th anniversary of the disaster, the city unveiled a memorial plaque at the site where the tank stood – now Langone Park on the North End waterfront.

The Kennedys – an unprovable bootlegger legend

No story of Prohibition in Boston is complete without mentioning the Kennedy family. Legend has it that Joseph P. Kennedy Sr. – the father of future president JFK – made his fortune smuggling alcohol from Canada during Prohibition. This is one of the most enduring legends of American politics. And one of the hardest to verify.

What we know for sure

The documented facts are as follows. After the repeal of Prohibition in December 1933, Kennedy founded Somerset Importers, which immediately obtained exclusive rights to import several prestigious alcohol brands – Haig & Haig, Dewar's, and Gordon's Gin. The contracts were ready at the time of the repeal, suggesting that Kennedy negotiated them much earlier.

Within a few years, Somerset Importers made Kennedy one of the richest men in America. He used this fortune to fund the political careers of his sons – including the presidency of John F. Kennedy.

What we do not know

The allegation of bootlegging – that Kennedy smuggled alcohol from Canada while Prohibition was still in effect – has never been proven. There are no court records, no indictments, no direct evidence. Historian Daniel Okrent, author of the monumental work Last Call: The Rise and Fall of Prohibition, examined this issue in detail and concluded that the evidence is "at best anecdotal".

The legend of the Kennedy bootlegger has survived for several reasons. First, it fits the myth of a family that rose to power by any means necessary. Second, the fact that Kennedy had ready import contracts on the day Prohibition was repealed is suspiciously convenient. Third – and perhaps most importantly – Kennedy never publicly denied these rumors, which some interpret as a silent admission and others as a wise political strategy.

The truth is that Joe Kennedy was primarily a financial genius who could foresee the end of Prohibition and prepare for that moment. Did he start earlier than he could legally? Maybe. But there is no evidence.

Gustin Gang – the Irish mafia of the Boston waterfront

While Italians and Jews ruled in New York, and Al Capone built his empire in Chicago, Boston was an Irish city. And the gangsters were Irish too.

Gustin Gang – named after Gustin Street in South Boston (“Southie”) – controlled the smuggling and distribution of alcohol in the southern part of the city and on the waterfront. At the helm was Frank Wallace, a charismatic boss who built his organization on the hard loyalty of the Irish community in Southie.

Control of the waterfront

Wallace's gang profited from three sources. First – smuggling alcohol by sea. The Boston waterfront was an ideal unloading point for ships bringing whiskey from Canada, rum from the Caribbean, and even gin from Europe. Second – protection of speakeasies in South Boston and surrounding areas. Establishment owners paid a "fee" in exchange for the guarantee that gangsters would not rob them (and that they would warn them of federal raids). Third – extortion against other criminal groups trying to operate in their territory.

The Hanover Street Massacre

On December 22, 1931, Frank Wallace went to a meeting at 317 Hanover Street in North End – a neighborhood dominated by the Italian mafia. It was supposed to be a peace meeting to resolve ongoing tensions between the Irish and Italian crime groups.

It was a trap. Wallace and his associates were shot as they entered the establishment. Wallace's death shifted the balance of power in Boston's underworld – from Irish gangsters to the Italian mafia, which dominated organized crime in the city for decades to come.

However, the tradition of the Irish gang survived in another form. The Winter Hill Gang from Somerville – whose most famous boss was later Whitey Bulger – continued the Irish tradition of organized crime in Boston until the end of the 20th century.

Harvard and Prohibition – 78% of students drank

Harvard University – the oldest and most prestigious institution in America – was one of the most "wet" places in Massachusetts during Prohibition. A study conducted in 1920, just a few months after the ban took effect, found that 78% of Harvard students drank alcohol.

“Gold Coast” and Harvard Square speakeasies

The wealthiest Harvard students lived in luxurious homes on Mt. Auburn Street – in the so-called “Gold Coast.” Private parties with an abundance of illegal alcohol were the norm. An invitation to a party hosted by the “Gold Coast men” was one of the most sought-after in Boston.

Several speakeasies operated around Harvard Square serving students and faculty. The academic staff and university administration largely turned a blind eye to students drinking – as long as they did not cause public scandals. The approach was purely pragmatic: trying to enforce the ban on campus would result in mass expulsions of the brightest students from the wealthiest families.

The academic paradox

Universities across America conducted economic and sociological studies proving that Prohibition did not work. Harvard professors – including prominent economists and lawyers – publicly criticized the ban as ineffective, unjust, and harmful. And then they went for a drink at one of the nearby speakeasies.

This was not hypocrisy – it was a logical consequence of the belief that the law was wrong and should be changed. Many professors actively engaged in the movement to repeal the 18th Amendment while simultaneously breaking it on a daily basis.

Locke-Ober – from 1875 to speakeasy and back

Few restaurants in America have a history as colorful as Locke-Ober at 3 Winter Place in downtown Boston. Opened in 1875, it quickly became a favorite restaurant of Boston's elite – politicians, professors, financiers, and artists.

Silver Dollar Bar and “Yvonne”

A legendary feature of Locke-Ober was the Silver Dollar Bar on the ground floor – with a bar lined with silver dollars and a huge painting of a naked woman hanging behind the bar. The painting was titled “Yvonne” and became an icon of the establishment. Tradition dictated that every time the Harvard Crimson baseball team lost to rivals from Yale, the painting “Yvonne” was covered with mourning crepe.

When Prohibition came, Locke-Ober exploited a legal loophole and transformed into a private club. In theory, alcohol was not served – in practice, regular patrons drank as before. Only the formal status of the establishment and the need for "membership" changed.

137 years of history

Locke-Ober survived Prohibition, the Great Depression, two world wars, and dozens of changes in the Boston dining scene. It ultimately closed in 2012 after 137 years of operation.

But the story does not end with its closure. In the same building at Winter Place, Yvonne's – a modern cocktail bar named after that famous painting – operates today. The circle has closed.

Boston Harbor – smuggling from Canada to the Caribbean

If New York had Rum Row, Boston had something even better – the entire Atlantic. The city's location on the northeast coast made it an ideal destination for smuggling routes from three directions.

Rum Row off the New England coast

Rum Row – a fleet of ships standing just outside the territorial waters of the USA and selling alcohol to smaller boats that delivered it to shore – was more active off the New England coast than off New York. The waters from Cape Cod to Maine were teeming with fishing boats that unloaded crates of whiskey and rum in addition to fish.

Three smuggling routes

Alcohol reached Boston via three main routes:

• From Canada (Nova Scotia and New Brunswick) – the shortest and most common route. Canadian law allowed for the export of alcohol, so whiskey was legally sold in Halifax or Saint John and then smuggled by boats to Massachusetts.
• From the Caribbean – rum from Jamaica, Cuba, and the Bahamas arrived on trading ships. Some was hidden in legal cargo, while some was transported by dedicated smuggling ships.
• From Europe – gin from England, wine from France, whiskey from Ireland and Scotland. Transatlantic passenger ships regularly carried alcohol hidden in passengers' luggage and in the holds.

“Prohibition Navy” – a losing battle

The Coast Guard patrolling Boston's waterfront and Massachusetts Bay was chronically underfunded. The few agents had slower boats than the smugglers and were unable to monitor hundreds of miles of coastline. It is estimated that they intercepted no more than 5% of smuggled alcohol.

What you don't know about Prohibition in Boston

Every city has its secrets from the Prohibition era. Here are Boston's – lesser-known but equally fascinating.

Police officers owning speakeasies

Several Boston police officers were arrested and convicted for running their own speakeasies. It was not about turning a blind eye to others breaking the law – they literally ran illegal bars, using their position to warn each other of federal raids. One of them explained in court that a police officer's salary was not enough to support a family – which was true, but the court did not consider it a mitigating circumstance.

Tunnel under Boston Common

One of Boston's more enduring legends speaks of a network of tunnels under Boston Common – the oldest public park in America – used to transport alcohol between speakeasies. Some of these tunnels do exist – they are old infrastructure channels from the 19th century – but their role in alcohol smuggling remains in the realm of urban legends.

Pharmacies selling more whiskey than aspirin

Like across America, Boston pharmacies exploited a legal loophole allowing the sale of alcohol by prescription. The number of prescriptions for “medicinal whiskey” in Massachusetts increased by 400% in the first year of Prohibition. Some pharmacies in the Back Bay and Beacon Hill neighborhoods were de facto liquor stores with a pharmaceutical sign.

Tea parties with a splash

Wealthy Boston ladies hosted “tea parties” – tea parties where tea was served with a generous splash of gin or brandy. This was socially acceptable because it took place “in good company” and behind closed doors. The reference to the Boston Tea Party – although this time the rebellion was not about throwing tea but about adding something stronger to it – did not escape anyone.

North End – “Little Italy” supplied wine

Italian residents of North End – a neighborhood adjacent to the port – specialized in producing homemade wine. The law allowed for the production of up to 200 gallons of wine per year for personal use. Many Italians interpreted this law very broadly – producing many times more and selling it to neighbors. The smell of fermenting grapes in North End was so common that federal agents did not even try to intervene.

Modern speakeasies in Boston

The tradition of hidden bars has returned to Boston in the 21st century. Modern speakeasies combine the aesthetics of the 1920s with contemporary cocktail art – and unlike their historical predecessors, they do not have to hide from the police.

Yvonne's

Address: 2 Winter Place, Boston (Downtown Crossing)

Located in the legendary space of the former Locke-Ober – a restaurant that was the heart of Boston's social life for 137 years. The interior is breathtaking – wood paneling, brass details, velvet sofas, and of course a tribute to the famous painting “Yvonne,” which hung here since the 19th century. The menu combines classic cocktails with modern “comfort food.” Reservations are recommended, especially on weekends.

Drink

Address: 348 Congress Street, Fort Point (Seaport District)

Drink has no menu. Literally. You sit at the bar, tell the bartender what you feel like – sweet, bitter, strong, refreshing – and you get a cocktail created just for you. This radical concept earned the establishment a James Beard Award – the “Oscar” of American gastronomy. The underground space, brick walls, and intimate atmosphere. They do not take reservations – you just have to come and wait in line. It’s worth it.

Backbar

Address: 7 Sanborn Court, Union Square, Somerville

Hidden behind the restaurant Journeyman – you have to walk through a narrow courtyard (Sanborn Court) and look for unassuming doors. Inside – a cozy space with craft cocktails that change seasonally. Backbar is technically in Somerville, not Boston, but it lies just outside the city border and is considered one of the best hidden bars in the entire metro area. The atmosphere is more casual than downtown – perfect for a longer evening.

Hecate

Address: 2 Boylston Place, Boston (Theatre District)

Hidden in a narrow alleyway, Boylston Place – you have to know where to look. The theme of witchcraft and the occult refers to the darker chapters of New England's history (Salem is not far away). The dark interior, candles, and mysterious cocktails with names referencing mythology make it one of the most atmospheric speakeasies in the city.

Extra Dirty

Address: Back Bay, Boston

A bar specializing in martinis – in dozens of variations. If you love martinis, this is your place. If you don’t like them – you might change your mind. An elegant, minimalist space in the exclusive Back Bay neighborhood. The name refers to “extra dirty martini” – the version with a lot of olive brine.

89 Charles

Address: 89 Charles Street, Boston (Beacon Hill)

In the basement of a historic building on Beacon Hill – one of the oldest and most picturesque neighborhoods in Boston. Classic speakeasy vibe – low ceilings, brick walls, dim lighting. A narrow staircase leading down adds authenticity. The cocktail menu combines classics with seasonal offerings. Beacon Hill in the evening – with gas lanterns and cobblestone streets – is the perfect backdrop for a visit to a hidden bar.

Tips for visitors

Boston is one of the easiest large cities to explore in America – a compact center, excellent public transportation, and a wealth of history at every turn.

Prohibition Trail – walking through history

The best way to learn about Boston's Prohibition history is to take a walk combining the Freedom Trail with places related to the alcohol ban:

1. Start: Langone Park (North End) – the site where the Purity Distilling Company tank stood. A memorial plaque from 2019.
2. North End – the Italian neighborhood where homemade wine flowed freely. Walk down Hanover Street to number 317, where Frank Wallace was shot.
3. Faneuil Hall and Quincy Market – the official Freedom Trail route, but also an area where numerous speakeasies operated.
4. Winter Place – Yvonne's in the former Locke-Ober space. You can stop by for a cocktail.
5. Boston Common – the oldest public park in America, under which supposedly run old smuggling tunnels.
6. Beacon Hill – 89 Charles for an evening drink in the basement of a historic building. Cobblestone streets and gas lanterns create the perfect atmosphere.

Transportation – T (subway)

The Boston subway (known as the “T”) is the oldest subway system in America (1897). Main lines:

• Green Line – runs through Back Bay, Beacon Hill area, and Cambridge (Harvard)
• Red Line – South Station, Fort Point (Drink), Harvard Square, Somerville (Backbar)
• Orange Line – Downtown Crossing (Yvonne's), Chinatown, Theatre District (Hecate)

Most speakeasies in the downtown area are within walking distance from T stations. Single tickets cost $2.40 (CharlieCard) or $2.90 (CharlieTicket/Apple Pay).

When to go

The best time for a “speakeasy tour” in Boston is autumn (September–November) – beautiful leaf colors, moderate temperatures, and fewer tourists than in summer. Avoid the week around Patriots' Day (the third Monday in April) and the Boston Marathon – hotels are expensive and full during that time.

Practical tips

• Reservations: Yvonne's and Hecate – definitely yes. Drink and 89 Charles – do not take reservations, you have to wait. Backbar – optional.
• Dress code: Boston speakeasies are less formal than New York ones. Smart casual is sufficient everywhere. You can come in jeans to Drink.
• Cocktail prices: $14–$20 in most establishments. Drink is slightly more expensive due to the personalized approach.
• Tips: Standard 18–20% in Boston. Bartenders in speakeasies are craftsmen – it’s worth appreciating their work.
• Harvard Square: If you have time, visit the Harvard campus (Red Line to Harvard station). Admission to the campus is free. Imagine students returning from an illegal bar in 1925 along the same paths.