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 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.

Plan a visit & invite your people →

Further reading: visitindy.com · do317.com

last checked: 2026-07-21