938 N Cook St., 517-9931, libertyglassbar.com. 3 pm-2:30 am daily.
Liberty Glass is a dimly lit cocktail bar in an old house at the base of North Mississippi Avenue, so of course it's the best least-kept secret among throngs of Internet daters in Portland proper. "It has a clawfoot tub in the bathroom!" you'll say to yourself as you negotiate arrangements to meet a total stranger for the tail end of a happy hour on a weeknight. How will this not be impressive? But there's more at stake here than being cool by proxy. This may be one of the coziest, most unpretentious cocktail spots in the entire city, and you will not regret a single minute spent here. The drinks are strong, inventive and worthy of twice the markup in more cosmopolitan markets such as New York or San Francisco. Then again, where on earth would you find a drink made with Earl Grey tea, whiskey and fernet and a Naugahyde booth atop creaky floorboards in which to consume it? Oh, yeah: in a tiny house across from an empty lot with a tire swing, at the bottom of a hill in Portland. That's where.
Happy hour: 3-6 pm daily. $1 off taps and specialty cocktails.
Entertainment: Monday night bingo (8:30-10 pm) brings out NoPo's tragically hip and unrepentantly raucous gamblers. Good-luck trinkets welcome—but easy on the candles, Smokey.