21 Vintage Photos of Prohibition Speakeasies in the 1920s

History Vintage Photos May 1, 2025

Last Updated on May 1, 2025 by Colby Droscher

In the 1920s, Prohibition made alcohol illegal across the U.S., but that didn’t stop people from finding ways to drink. Hidden behind bookcases, in basements, or through secret alleyways, speakeasies became the go-to spots for those chasing a good time. With live jazz, flowing bootleg liquor, and a crowd that ranged from gangsters to flappers, these underground bars were alive with energy and defiance.

From shadowy backrooms to packed dance floors, these 21 vintage images reveal the grit, glamour, and rebellious spirit of a time when breaking the rules was part of the fun. I hope you’re ready to step back into the prohibition era, because here are 21 vintage photos of prohibition speakeasies.

1. The entrance to a speakeasy in 1921

Four people in 1920s attire stand next to a vintage car in a narrow alley. Two men and two women are talking and smiling near a sign reading, “All Sober Education To Who Enter Here.” Brick buildings line the alley.
salem-witch

That seems a bit obvious, but hey, if it works, don’t fix it.

2. This is how speakeasy owners hid the liquor

Black and white photo of a woman standing outdoors; on the left, she wears a long patterned coat, and on the right, she wears a short dress, holding two cans with straps, revealing her legs above the knees.
watsin_aname

I wonder if her body temperature made the liquor warm.

3. That’s quite the juxtaposition

A group of people at a table smiling and drinking, holding a sign that reads, “In compliance with the 18th Amendment, no intoxicating liquor allowed on the premises.” Various bottles are on the table.
mrtrousers14

As you can see, these people take the rules very seriously.

4. Drinking at Raceland, early 1930s

A group of people, including men and women, sit at a bar drinking from bottles. They appear lively and cheerful. There are posters and a large fan on the wall behind them. The setting looks vintage, possibly from the early 20th century.
jrs5682

Raceland was a Louisiana speakeasy. It surprises me that people are okay having their photos taken while doing an illegal act.

5. Irish pub speakeasy in New York City, 1933

Black and white photo of a busy bar, with men in coats and hats standing at the counter and sitting at tables. A bartender serves drinks while groups converse in a lively, vintage setting. LIFE magazine watermark is visible.
userdeleted

This guy on the left gets it: hide your face when someone tries to incriminate you.

6. Hanging out at the Krazy Kat Club

Three people sit on chairs around a table on a wooden platform built in a tree, surrounded by large branches; a brick wall is visible in the background. The image is in black and white.
laceandhoney

This 1920s speakeasy had a treehouse in the back where you could indulge yourself with alcohol.

7. Inside a San Francisco speakeasy, 1931

Black and white photo of four men in suits and hats standing at a bar counter, while a bartender in a vest serves drinks. The bar has ornate woodwork, mirrors, and glasses neatly arranged.
userdeleted

The name was the House of Shields, and it has a creepy story of a president passing in the basement.

8. Raiding a Boston speakeasy, 1920s

Five men stand in a cluttered room filled with boxes, bottles, and other items. They look toward the camera, with two of them holding a large mirror. The room has dim lighting and decorated walls in the background.
5_frog_margin

Local police and federal agents would go undercover and get served at a speakeasy. Once they knew there was alcohol, law enforcement officials would seize the alcohol and destroy the bar.

9. Ladies’ night at a 1920s speakeasy

Four women in 1920s flapper dresses and hats sit at a bar, smiling and holding drinks, with two men in suits on either end. The scene is lively, set in a vintage barroom with framed photos on the wall.
endersgame_reviewer

Bring back these legendary hats.

10. She’s taking some to go

A woman in a 1920s dress and cloche hat sits by a table, smiling as she adjusts her garter, revealing a flask strapped to her thigh. Flowers and candles are on the table.
azrat2012

The penalty for possession of alcohol was a swift $1000 fine and/or up to 6 months in jail. And that’s just for the first offense.

11. A family at a Boston speakeasy in 1931

A black and white photo shows five people in 1930s attire gathered at a bar. Two men in suits sit on stools, while a woman in a dress and two men stand nearby, all appearing relaxed and cheerful.
rfs12307

This was taken just 2 years before prohibition ended. Imagine having to pay $1000 just for alcohol to become legal 2 years later.

12. Another view of the Krazy Kat’s treehouse

Five young women in vintage clothing relax in a rustic treehouse, sitting on chairs and a bench built among large tree branches, with sunlight filtering through the leaves. They appear to be socializing and enjoying each other's company.
watsin_aname

The club became too hot in the summer, so they offered this small area for outdoor seating when it got too hot.

13. This speakeasy was on Waterloo Avenue, Cleveland, Ohio, 1920s

Two men in suits and hats lean close together at an empty bar counter in a dimly lit, old-fashioned tavern. The scene suggests a secretive conversation in a vintage or historical setting.
myipodstillworks

These men can’t be fooled. They knew to hide their heads when someone came around with a camera.

14. A Budweiser speakeasy in Breckenridge, Texas

Black-and-white photo of a vintage bar with men standing at a counter, bartenders serving drinks, shelves of bottles in the background, and a waiter in white uniform near stacked cases. Ceiling fans and wall art are visible.
axlcobainvedder

Leave it to Budweiser to open a speakeasy the same year prohibition started, 1920.

15. This was a Boston speakeasy on Causeway Street, 1932

Four men stand inside a bar, smiling and holding boxes and containers. The floor is scattered with boxes and bottles. Murals of musicians are painted on the wall behind them.
ryansmith

It was raided and destroyed by federal agents just one year before prohibition ended.

16. Federal agents hauling kegs out from a speakeasy cellar

A group of men in suits and hats work together to remove barrels from a sidewalk outside a storefront, using ropes and teamwork, while several others look on. The scene appears to be from the early 20th century.
axlcomainvedder

Since profits were so high, most speakeasies opened back up just a few days after they were raided.

17. Having some fun during prohibition in Hot Springs, AR

Sepia-toned photo of two men outside a rustic "Saloon" with bottles and humorous signs, including “Don’t Drink Prohibited Liquor—Have a Good Drink,” and “Dave’s Place.” One man drinks from a jug labeled "Moonshine.
alrightguyuk

This was a place people could take gag photos with fake booze.

18. That’s a lot of liquor

A black-and-white photo shows men in early 20th-century clothing standing among numerous boxes and bottles, likely during Prohibition, in front of stacked crates filled with alcohol containers.
dhorlin

Most speakeasies bribed cops to tip them off when a raid was coming, these guys must not have gotten a hint.

19. Hiding the personal stash in Harlem, 1932

A woman and man in fur coats stand beside a classic car parked on a city street with brownstone buildings in the background; the car door is open and the man sits inside. Photo appears to be from the early 20th century.
notbob1959

The best way to hide your booze is in a massive fur coat.

20. A Chicago speakeasy during prohibition, 1920s

A group of well-dressed men and women at a crowded bar smile and raise drinks as a bartender in a white uniform shakes a cocktail shaker, creating a lively and festive atmosphere.
jalbert653

Everyone looks so happy and connected.

21. Celebrating the end of prohibition, 1933

A group of people raise beer mugs at a bar beneath a sign that reads "Farewell 18th Amendment," celebrating the end of Prohibition; the bartender stands behind the counter, also holding a drink.
otherwisetackle5219

This speakeasy was open anyway, but people will do anything to celebrate.

Do you want to see more prohibition content?
Check out these 20 Photos of Prohibition-Era Bootleggers in Action, or step back into the years of prohibition with 31 Photos From Prohibition (1920-1933) That Perfectly Capture the Chaos of the Time. If you want to check out the oldest bars in America, take a look at these 15 Old School Cowboy Saloons That Still Exist Today.

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