Circa 33, Portland
How to get in:
Enter the code in the "mafia" book on the shelf by the bathrooms in the Circa 33 building, enter the speakeasy, play some pool.
Circa is accessed via a clandestine bookshelf, because that's the best way ever to access things. One room hosts pool tables and darts (obviously pretty rare for these kinds of places), and the other has seating and live piano entertainment. They even have food, and all their on-menu drinks follow a specific "classic formula" of spirit + sugar + citrus + bitters, but you can, of course, deviate if you want a more personalized experience.
What you're drinking:
Check out the Planters Punch, which combines dark rum, lime juice, Angostura bitters, nutmeg, sugar, and mint.