20 Best Bars in Portland, Maine, for Hole-in-the-Wall Dives, Sceney Cocktail Lounges, and Waterfront Wine Bars


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Portland, Maine, has undergone a significant transformation in recent years, and its bar scene is a perfect reflection of this change. The city’s historic charm has given way to a more modern and vibrant atmosphere, with a wide range of bars and lounges catering to different tastes and preferences.

20 Best Bars in Portland, Maine, for Hole-in-the-Wall Dives, Sceney Cocktail Lounges, and Waterfront Wine Bars
Source: media.cntraveler.com

One of the standout features of Portland’s bar scene is its rich history. From the historic General Lafayette House to the trendy cocktail lounges, each bar has its own unique story to tell. The General Lafayette House, for instance, is a nod to the city’s colonial past, while the trendy cocktail lounges are a testament to its modern appeal.

20 Best Bars in Portland, Maine, for Hole-in-the-Wall Dives, Sceney Cocktail Lounges, and Waterfront Wine Bars
Source: media.cntraveler.com

Best Bars in Portland

Here are some of the best bars in Portland, Maine, that offer a unique experience:

20 Best Bars in Portland, Maine, for Hole-in-the-Wall Dives, Sceney Cocktail Lounges, and Waterfront Wine Bars
Source: media.cntraveler.com

Elizabeth’s

Located in the heart of Old Port, Elizabeth’s is a cosmopolitan zinc bar that offers a dreamy party atmosphere. The bar is adorned with thumping tunes, dim lighting, and a powerful deep crimson from overhead and in glossy graphics. The wine list is impressive, with a plentiful spectrum of whites running the gamut of prices, from the formidable Sylvain Langoureau Chardonnay to a crisp Joseph Cattin Alsace Riesling. The compact cocktail program is like the vibe here: down for fun.

The American Amour, which is described as ‘like a post-coital cigarette,’ doesn’t quite deliver on that ambitious promise but satisfies nonetheless, with a hit of mezcal, vermouth blanc, apricot liqueur, and Suze—the bittersweet French aperitif.

Benny’s

Benny’s is a high-energy neighborhood joint that offers a swirl of Italian-American culture’s greatest retro hits. The bar is adorned with vintage photos smatter the walls, sports trophies shine over the door, and jars of pickled peppers and tomatoes crowd the back bar shelves. The retro Italian-American theme may not take itself too seriously, but that doesn’t mean everything isn’t tasty.

There’s an entire section dedicated to Campari concoctions, from the beloved Americano (with sweet vermouth, and seltzer) to the house Negroni (with Goldie’s Gin and sweet vermouth). Fun signatures include ‘Benny’s Dirty Martini,’ with house-made Giardiniera brine—as in, the classic Italian relish—with gin and olives, and the ‘Italian 76,’ a bubbly combo of gin, limoncello, Strega, and prosecco.

About five each of (all Italian) reds, whites, and sparkling options are available by the bottle or glass, nicely chosen and fairly priced. Beers run from serious and local (Austin Street Patina Pale Ale) to thematically appropriate (Miller High Life) and just plain silly (PBR & a shot of whiskey).

Lucky Cheetah

Lucky Cheetah is a subterranean dumpling lounge that offers a fearless pan-Asian-globalist maximalism. The bar is adorned with crystal chandeliers and bright lanterns hovering above the red brick-meets-marble-meets-gold-meets-red lacquer bar. Everything about this bar is unapologetically over-the-top, and it’s a complete blast.

The wine list is perfectly sufficient, but it’s the exceptional cocktail game and Champagne list that take center stage at Lucky Cheetah. The latter boasts a list of more than ten labels, and can run as mightily priced as a bottle of Aubert et Fils Brut from Eperney, or quite earthly (and still excellent) with Italian Fiol prosecco. All are offered by the glass, as well.

Cocktails, creative as they are, run the gamut from classic to innovative, with options like the ‘Spicy Mango Margarita’ and the ‘Cucumber Gimlet.’ Each cocktail is expertly crafted with the finest ingredients and presented with flair.

From the historic General Lafayette House to the trendy cocktail lounges, each bar in Portland has its own unique story to tell. Whether you’re looking for a hole-in-the-wall dive, a sceney cocktail lounge, or a waterfront wine bar, Portland has something for everyone.