Midnight Cowboy

When a former brothel is reincarnated into a speakeasy-style luxury cocktail lounge, you know there is fun to be had. The Midnight Cowboy is hidden in plain sight amongst the obsceneties of Dirty Sixth, and can only be identified by the authentic "Midnight Cowboy Oriental Massage" sign that hangs above the unassuming second-story establishment. Once inside this reservation-only drinkery, the dim lighting, low music, and fabulous cocktails set the mood for an inimate evening with friends and conversations about the building's sleazy past. The "massage" rooms in the back can be reserved for parties of six to eight, so there's that.

Reservations can be made online, which is the least authentic aspect of the experience. The rest is straight-up Prohibition Era. Once you arrive at 313 East Sixth Street, press the buzzer marked "Harry Craddock" and a friendly host will take you upstairs. Reservations are for two hour blocks and there is a two drink minimum per person. Make sure you order your last round of drinks with enough time to enjoy them because when your time is up, they'll kick you out.