In the 1920s and 1930s, Indianapolis played stomping grounds for a number of notorious gangsters — most famously John Dillinger — and the city is now home to numerous speakeasy-inspired establishments.
If you’ve been around for any length of time, you know I’ve never met a Prohibition-Era spot I don’t love. However, one Indy speakeasy still operates in a more authentic fashion than all the rest.
Most locals have heard of Bootleggers but finding it is another task altogether.
The address of the speakeasy isn’t advertised online, and there’s certainly no website or Google Business listing for the bar. In fact, just like in the Roaring Twenties, the only way to get into Bootleggers is to know someone in the know.
When we finally learned exactly where Bootleggers is (and what the entry password is) I couldn’t wait to visit. The experience was just as authentic as I expected it to be. You’re in for a treat when you get the chance to go.
Upon finding the right door to the basement — a job in and of itself — you’ll turn an antique brass key to reveal the speakeasy’s gatekeeper. Say the secret password and you’re in!
Once you’ve gone down the stairway, you’ll be met with an incredibly authentic speakeasy experience. While some of the seating areas have contemporary furnishings, the bones of Bootleggers are anything but. You won’t find sleek paneling and ornate artwork here.
Instead, imbibers are surrounded by the building’s original stone foundation, with brick walls scattered throughout.
In a restaurant culture where speakeasies have become glamorized, there’s no glitz and glamour at Bootleggers — and, frankly, that makes it all the more fun.
Real Prohibition speakeasies made do with what they had in basements or back rooms. This is as close as you’ll come to the real thing 100 years later.
And, while the bartenders aren’t slinging actual bathtub gin, you can order from a selection of era-appropriate cocktails, including Old Fashioneds, Negronis, Gin Rickeys, Manhattans, and Sidecars.
As you can see [below], Bootleggers has a full bar, so if you’re in the mood for a 21st century drink, you can order that as well.
I highly recommend chatting with the bar staff if you get the chance. Everyone I spoke to was well-versed in the history of the establishment above Bootleggers. You’ll have the opportunity to hear some incredible tales.
If you’re sold on spending your next night out pretending you’re with Lucky Luciano or Al Capone’s outfit, Bootleggers is the place for you.
P.S. With Valentine’s Day approaching, it’s also a surprisingly good spot for a date night.
For a hint about the location and the password, follow me on Instagram (@_rebekahbarton) and send me a DM. Can’t wait to hear from you soon!
I don’t have insta, but would love a hint nevertheless! Surprising hubs with a babysitter and a date for Valentine’s Day and he has no idea. This would be such a cool thing!
I can’t post publicly but I am emailing you the hint!
Can you email me a hint as to the location?
This would be such a cool surprise for my wife…and me.
Thanks!
Yes, I will send!
Does the password change often? If not, please send! Love this!!
I have been told the password will be the same for the foreseeable future. Sending you an email! You can also follow along for more travel/speakeasy adventures if you have Instagram @_rebekahbarton
Any help on the password? I found the location. This place looks great. Thanks!
Emailing you! So sorry for my delayed reply. I’m just back from vacation today.
Are you still sending email hints? Will be downtown this weekend and this would be an amazing surprise for our group!
Emailing you! So sorry for my delayed reply. I’m just back from vacation today.
Could you email me the hint as well?
Emailed you!
I would LOVE the hint as well!!! Will you PLEASE email me, too ?!?!
♡♡♡♡♡♡
Emailed you!
Such a fun read! Would love a hint, as well (and am similarly IG-less), please! 💌
Thank you, Nikki! Sending you an email as well!
Sounds like somewhere me and my lady would enjoy. Could we speak more privately?
Hi Rebekah I sent a dm I have some friends from out of town that I think would love the experience of finding it. I can also give you an email as well. Thank you!
Hi Luke — hope you guys have a blast!
This speak easy looks amazing and the mystic about the place is intriguing! would luv the password to come enjoy ur speak easy.
Emailed you!
I am heading there for my 40th tonight and would love a hint! I followed you on IG but didn’t know where to find it! Thanks!
Hi Tiffany — hope you guys have a blast! Just shoot me a DM on Insta if you need any help!
Hi,
Hubs and I would love a chance to get to see this awesome place! We are only here until end of March for work!
Hi! Yes, reach out on Instagram @_rebekahbarton. If you don’t have Instagram, I can send you an email.
Me and my wife were trying to check it out? Anyway I would be able to receive a hint? I know the location but not the password?
Hi! Yes, reach out on Instagram @_rebekahbarton. If you don’t have Instagram, I can send you an email.
Lgscrogham@yahoo.com.
Would love to visit can you send me a hint to the Bootleggers please?
Yes, I will send!
Could you send me a hint to my email? Would love to try it out for my birthday. 🙏🏼🙏🏼
Of course!
Hello, I would love an email. Tonight is my husbands birthday and we would love ti have the experience
Hi! So sorry I just saw this. Your email is not listed! If you have Instagram, you can reach out @_rebekahbarton. Otherwise, feel free to email at rebekah.barton88@gmail.com. 🙂
Such a great and fun read! I am new to the city and trying to find and visit all the of speakeasies in Indianapolis. I have visited only 2 so far and I loved them! The history and the aesthetic were top-notch. I can not wait to visit more and read about your fav Indy spots.
Will you please send me a hint via Insta (I messaged you there as well) or via email? Thanks again for this blog:-)
Hi Stephanie! So glad you’re here and thanks for following along on Insta!
Hey there! I have a birthday coming up and would love to visit this speakeasy! Can you send me a hint via my email please and thank you!!
Yes, I will send!
This would be such a cool date night idea! I would love a hint if you could send me one!
Sending you an email! You can also follow along for more travel/speakeasy adventures if you have Instagram @_rebekahbarton
Would love to visit this speakeasy with my husband for his birthday. Please send me the password. Thanks
Sending you an email! You can also follow along for more travel/speakeasy adventures if you have Instagram @_rebekahbarton
I would love to take my GF who just recovered from Cancer as a surprise. It’s on her bucket list! Hint would be so appreciated!
Sending both of you all the best — will shoot you an email! You can also follow along for more travel/speakeasy adventures if you have Instagram @_rebekahbarton
Going for an anniversary trip this weekend; would love a hint!
Sending you an email! You can also follow along for more travel/speakeasy adventures if you have Instagram @_rebekahbarton
Love the Speakeasy vibe & always wanting to try something new close to home. Just heard of Bootleggers last night & while I don’t have Insta (even though everyone tells me I should, lol), I would love a hint on Location & any password info. you may be willing to provide. Email always available!
Emailing you! Also highly recommend Insta (I’ll be posting from Scotland and Ireland — including speakeasies — all next week)
Ahhhhh I want this for my birthday! Please send me a hint <3
Emailing you! So sorry for my delayed reply. I’m just back from vacation today.
I would love a hint on the password!
Emailed you!
I’d like to check them out for my b-day. Do you mind sharing the location and password?
Emailed you!
My wife and one of her long time girlfriends are looking to go somewhere different and have mentioned a speakeasy. Any chance at a few hints I could give her to find it would be great and help gain me some hubs points. 😅. Thanks
We would love the password. We live downtown and this would be an amazing date night.
Emailed you!
I do not have insta-gram, I would love a hint to the location, and the password. Thanks
Emailed you!
Hello, my husband and I seen a segment on the Indy Now show this morning. Bootleggers looked like it would be a very intriguing place to visit. We always look forward to great new adventures! Help with hints on the location and password would be greatly appreciated! Thank you in advance! I don’t have Instagram.
Emailed you!
Hello Rebekah, straight from Al Capone’s stomping grounds in Cicero (Chicago). Will be in Indy early April. Any way I could get the location and Password for me and my gal? Thanks
Of course — emailed you!
Would love to take my Husband.
He will love this place!
Can you please send any hints on location and password?
Thanks!
Emailed you!
Hey! Loved your article 🙂 Moved downtown about 9 months ago and would love a hint to the password if you’re able 🙂
Thanks! Emailed you!
My Wife and I will be in town this weekend and this sounds like a fun date thing to do, However we do not know the area and would definitely need some hints? As to where to start etc.
Emailed you!