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
That seems a bit obvious, but hey, if it works, don’t fix it.
2. This is how speakeasy owners hid the liquor
I wonder if her body temperature made the liquor warm.
3. That’s quite the juxtaposition
As you can see, these people take the rules very seriously.
4. Drinking at Raceland, early 1930s
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
This guy on the left gets it: hide your face when someone tries to incriminate you.
6. Hanging out at the Krazy Kat Club
This 1920s speakeasy had a treehouse in the back where you could indulge yourself with alcohol.
7. Inside a San Francisco speakeasy, 1931
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
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
Bring back these legendary hats.
10. She’s taking some to go
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
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
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
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
Leave it to Budweiser to open a speakeasy the same year prohibition started, 1920.
15. This was a Boston speakeasy on Causeway Street, 1932
It was raided and destroyed by federal agents just one year before prohibition ended.
16. Federal agents hauling kegs out from a speakeasy cellar
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
This was a place people could take gag photos with fake booze.
18. That’s a lot of liquor
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
The best way to hide your booze is in a massive fur coat.
20. A Chicago speakeasy during prohibition, 1920s
Everyone looks so happy and connected.
21. Celebrating the end of prohibition, 1933
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.