Weekend: When Being the Host Becomes a Burden 😒

Come for the Lobster Rolls, Stay for the Small Town Charm in This New England Coastal City

theSkimm

While some may refer to it as the “other Portland,” we like to think that Maine’s biggest city stands out in its own right. Known for buttery lobster rolls and postcard-worthy lighthouses, Portland is also home to a thriving artistic community, award-winning restaurants, and bustling downtown area. (If you’re driving, be sure to swing by this century-old general store.) And did we mention it has more microbreweries per capita than any other city in the world? Bottoms up.

🛏 Housed in the former headquarters of the Portland Press Herald, Maine’s biggest newspaper, the Press Hotel is a contemporary tribute to its historic journalism roots. Not only does the luxury boutique hotel boast a two-story typewriter installation and walls covered with old news copy, each of the 110 guest rooms are inspired by 1920s writers’ offices and feature a vintage-style writer’s desk, wood floors, and local artwork. Speaking of, don’t forget to check out the hotel’s impressive art gallery, which is open to the public and spotlights major artists from the area.

⚓ Spend an afternoon wandering the cobblestone streets of historic Old Port. Lined with salty wharves and fishing piers, the district is packed with art galleries, restaurants, breweries, and funky shops. (Pop into Portland Trading Co. for unique homegoods, Portland Dry Goods for high-end clothing brands, and the 138-year-old Sherman’s Maine Coast Book Shop for, well, books.) Afterwards, walk over to the vibrant Arts District to see pieces by Claude Monet and Andy Warhol — in addition to over 19,000 works — at the Portland Museum of Art, Maine’s oldest and largest public art institution.

🌅 Portland is known for its stunning waterfront views. For some of the best, stroll the Eastern Promenade — a two-mile trail that’s part of a 78-acre historic public park — to get a 180-degree snapshot of Casco Bay. (If you get hungry watching the boats in the harbor, grab a bite from a nearby food truck.) And if you feel like getting in some extra steps, the promenade also connects to Back Cove Trail (tip: go at low tide for the best views of Portland’s skyline). Or, head 15 minutes south of the city to Fort Williams Park, where, in addition to breathtaking coastline scenery, you’ll also find the iconic Portland Head Lighthouse.

🍴 If you don’t eat a lobster roll did you really even go to Maine? There’s plenty of spots to choose from, but you can’t go wrong with local fave The Highroller Lobster Company (order the lobby pop — that’d be lobster on a stick) or Eventide Oyster Co., the buzzy James Beard Award-winning joint (warning: get there early to beat the line). If you need a break from seafood, try The Honey Paw for flavorful Asian-meets-New England dishes or Duckfat for their superb sandwiches and signature hand-cut Belgian fries (fried, of course, in duck fat). For fancier fare, nab a dinner reservation at Twelve — the same chef who headed up New York’s Eleven Madison Park — for elevated American cuisine.