Entry No. 18 — the Indianapolis file — filed under: speakeasy
Bootleggers
Located in the historic stone basement beneath The Flatiron at The Point on Penn, Bootleggers is a gritty Prohibition bunker that requires ringing a bell and giving a secret password.
The story
While most self-proclaimed speakeasies print their nightly door codes on Instagram stories and tuck themselves behind shiny photo-op bookshelves, Bootleggers refuses to run social accounts or place ads. It operates entirely out of the historic 1920s stone basement beneath The Flatiron building at The Point on Penn (605 N Pennsylvania St), relying on word-of-mouth and actual discretion.
Getting in isn't a matter of tapping a touchscreen. You have to hunt down the unmarked basement door, press the buzzer, and deliver the correct password through the door slot to whoever answers. If you show up clueless, you didn't hear it from us, but your best shot is pulling up a stool upstairs and prying a wordplay-heavy hint out of the restaurant staff.
Inside, the space drops all theatrical pretense. You're sitting in a low-slung, gritty Prohibition-style bunker surrounded by original raw stonework and exposed brick, drinking heavy, traditional cocktails far away from the street level.
What it's like
Head to the basement exterior door at 605 N Pennsylvania Street, hit the door bell, and be ready with the password when the door slot slides open. If you didn't do your homework, stop upstairs at The Point on Penn first for a drink and ask your bartender for a hint. Down below, expect a tight, dim space with low ceilings, rugged stone walls, and a menu focused strictly on classic, spirit-forward drinks.
The move: Find the unmarked basement door, ring the bell, and state the nightly password (ask the upstairs staff for a hint) to gain access to classic cocktails surrounded by original 1920s stonework.
- 📍 Downtown
- 💸 $$
- ⚡ Up for anything
- 🌗 Indoors
Where: 605 N Pennsylvania St, Indianapolis, IN 46202
Hours: Added 2026-07-21 — confirm current hours before you go.
⚠ Seasonal or scheduled — always check before you go.
Pair it with
- Wiseguy Lounge — Follow up a subterranean password test with another hidden door tucked behind a Mass Ave pizza joint.
- Chatham Passage — Walk five minutes south to stand over a subterranean street grate wafting fresh rose scent into the downtown air.
- Slippery Noodle Inn — Trade Bootleggers' hidden basement bunker for actual history at Indiana's oldest tavern, complete with genuine Prohibition ties.
- Verita Cocktail Lounge — Keep the basement bar crawl going by descending into another subterranean brick den tucked under Bocca.
Good to know
How do I get the password for Bootleggers?
Bootleggers doesn't post passwords online or on social media. You have to crack the wordplay yourself or ask the upstairs staff at The Point on Penn for a clue before ringing the basement bell.
Where is the entrance located?
Look for the unmarked basement door at The Flatiron building at 605 N Pennsylvania St in Downtown Indianapolis.
Do I need a reservation?
No reservations are taken, but entry relies strictly on ringing the bell, knowing the password, and having available space inside the basement bunker.
Plan a visit & invite your people →
Further reading: visitindy.com · do317.com · medium.com · Reddit
last checked: 2026-07-21