Don’t be fooled by At Random’s nondescript exterior. Inside you’ll find flaming drinks, “Mad Men”-era décor and absolutely no beer or wine. Try a Pink Squirrel, top-notch martini or Manhattan, the Tiki Love Bowl or an ice cream drink inspired by your favorite candy bar. It’s a true Milwaukee landmark and the scene of thousands of romances and heartbreaks over the years. Bring cash (no plastic!) and a designated driver.

At Random
2501 S. Delaware Ave.
414-481-8030

Runners-up (Cocktail Lounge): Bryant’s Cocktail Lounge, Hi Hat