It’s easy to miss this cocktail bar on Congress Street because there’s essentially no signage outside. Once you find it though, the Bearded Lady’s Jewel Box is one of the more interesting places to have a drink in Portland. There are candlesticks everywhere, an elaborate cocktail list on a silver framed menu, and white chiffon hanging from the ceilings, all of which make this place look like a Marie Antoinette-themed surrealist playground. But the best part of coming here is how helpful and knowledgeable the staff is, because if you’re going to drink something with hellfire habanero shrub bitters in a dark, loud room, you’re better off with a friendly bartender to guide you.
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Empire Chinese Kitchen
Empire in the Arts District is good for just about any occasion, with great Chinese food, cocktails, and an attached music venue.
Otto Pizza might have some interesting pies, like one with mashed potatoes, but we promise it will become your go-to pizza place regardless.
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Maps is a basement bar on Market St. where you’ll find vintage furniture, a vinyl collection your dad would envy, and plenty of beer.
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Central Provisions in the Old Port does small plates better than most, with a wide-ranging menu and a bar downstairs.
The Portland Hunt + Alpine Club
We’re not sure whether to call the Portland Hunt & Alpine Club a bar or a restaurant, but fortunately this Scandinavian spot works well as either.
Duckfat in Old Port is a tiny spot serving not-so-light dishes like poutine with duck gravy, brisket sandwiches, and milkshakes.
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