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The Coolest Things to Do in Portland, Maine

Part hipster, part prepster, with an old-world-meet-modern vibe, Portland, Maine is the ultimate East Coast weekend escape. You can find just about anything here, from one-off boutiques and standout restaurants to slick new bars and stylish hotels, not to mention the quintessential New England landscapes that look straight out of an Edward Hopper painting. We've rounded up our favorite things to do in the Pine Tree State's coolest city.

See recent posts by Sarah Pascarella

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At first glance, Portland’s Danforth Inn resembles your quintessential historic Maine home, a stately 1823 mansion that’s all aged brick and hanging ivy. Inside is something all together different. The main floor is an eclectic mix of quirky objects, lavish wallpaper, rich textiles and clean-lined furniture, with a Shanghai-inspired bar called Opium serving craft cocktails. At the hotel’s Southeast Asian restaurant, Tempo Dulu, guests gather to sample tasting menus made with decadent (and mostly local) ingredients delivered in portions that won’t overwhelm.

Another favorite hotel pick is the quirky Press Hotel, which debuted last year in the Old Port. Housed in the former home of the Portland Press Herald, the boutique property stays true to its past with journalism-inspired motifs everywhere, from the antique typewriters in the lobby to the custom wallpaper printed with newspaper headlines to the 110 rooms decorated like 1920s writer’s offices.

See all Hotels in Portland, Maine

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Eat and Drink

Owners Andrew Taylor and Mike Wiley’s Eventide Oyster Co. might have lines around the corner, but that shouldn’t stop you from checking out this creative seafood hotspot. Fresh-from-the-ocean dishes come in the form of tasty local oysters served with Tabasco ice and kimchi ice, various crudo small plates and a mouthwatering brown butter lobster roll.

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Don’t let the divey, no-frills look at ++J’s Oyster ++put you off. This seafood haunt is anything but basic. Located on a pier on Portland’s main drag (Commerce Street) and a favorite among tourists and locals, J’s has been serving unfussy classics since 1977. Belly up to their gigantic u-shaped wooden bar in the middle of the day and order their famous bucket of steamed clams, accompanied by a beer (or two).

The buzzy Street and Co. bistro is known for its wide selection of perfectly-cooked seafood dishes–from its small tasting plates to gigantic portions served in a pan, nothing disappoints. We recommend the Grilled Lobster on Linguine and Scallops in Pernod and Cream.

A newbie to the cocktail bar scene, Blyth and Burrows is a nautical-themed, three-bar-in-one concept with an ever-changing cocktail menu. On the first floor, you’ll find a main bar and seating area; the second level is all about oysters (and more libations); and in the basement there’s the speakeasy-style Broken Dram, which guests access through a secret entrance. Our favorite pours: the Death Stalker (vida mezcal, cilantro & poblano infused reposado tequila, yellow chartreuse, mango, chili, and lime) and the Delia Lea, a hot pink mixture of sumac infused vodka, suze, strawberry, shiso, persimmon and lemon.

RELATED: 8 Great Weekend Getaways in New England

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Portland has it fair share of tourist-trap gift shops, but it also offers one-off stores with truly unique wares. The men’s and women’s boutique Portland Dry Goods Co has a cooler-than-thou vibe but is still somehow unpretentious. Shop for wardrobe staples like high-quality leather goods, chunky fall sweaters and slick Barbour jackets.

From boxer briefs to shoe oil–and literally everything in between–the modern-day general store Portland Trading Co. is a blast to browse. Shop for everything you never knew you needed, including obscure apothecary items, coveted coffee table books, and funky dresses made by emerging designers.

The minimalistic boutique More & Co. looks like a highly-curated museum gift shop. We love their colorful porcelain objects, magical hair potions, and handmade wooden German toys.

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