Lobstering, Rare Beer, and Sunset Surfing: 4-Day Weekend in Portland, Maine

Portland Head Light
Sean Pavone / Shutterstock

No, not that Portland. Sure, there’s a booming craft beer scene, its share of hipsters and quaint locavore restaurants, but that’s where the parallels end. The original Portland (founded in 1786) is cozy at about a tenth the size of its West Coast counterpart, with more fresh lobster and restaurants per capita than almost anywhere else in the country. With a working downtown port, access to Atlantic, rivers, lakes, mountains, and trails, and the home of fleece-monger L.L.Bean, Portland’s the place to be. It’s time to drop the irony and head east.

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Old Port in Portland, ME
Old Port in Portland, ME jejim / Shutterstock


Set inside the former offices and printing plant for the Portland Press Herald newspaper, The Press Hotel is one of the city’s best spots to rest your head. The LEED-certified, beautifully designed boutique hotel offers 110 well-appointed spacious and light-filled guest rooms with city views, hardwood floors, incredibly comfortable beds, and a powerfully wonderful rain shower. Vintage artifacts from the former newspaper, as well as local mixed media art, can be found throughout. Its central location is within walking distance to everything downtown, from the Old Port to the West End and the Eastern Promenade (basically you don’t need a car and can walk everywhere—or borrow bikes from the hotel).

A solid alternative is the Old Port Regency Hotel & Spa, another boutique hotel in the middle of all the action. The hotel has more of an historic feeling while offering modern amenities like cozy bathrobes, marble bathrooms and fireplaces, and outdoor decks in some rooms.

If you fancy a chic B&B experience, you can’t pass up the Mercury Inn. Set in the Parkside neighborhood, this charming guesthouse lets you feel more like a local while getting pampered with daily breakfast items like housemade blueberry muffins and savory cheddar bread made with locally sourced ingredients.

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If you’re looking for good coffee, start your day at Tandem Coffee + Bakery. Set inside a former 1960s gas station, Tandem pumps out some of the best brew in town. Get one of their unique roasts and a pastry or opt for a malted iced coffee. Then walk up the street to Hot Suppa for breakfast of a pulled pork egg sandwich or go back for $1 oysters during happy hour Tuesday through Saturday from 4 to 6 p.m. If you want a classic spot (and need help with a hangover), hit the Porthole on the Old Port. Since 1929, this haunt has served fishermen and locals alike. Get the corned beef hash, indulge with the Casco Bay Omelet with Maine lobster and crabmeat or go at lunch for fish tacos and a cup of clam chowder. For quick, fresh-made sandwiches and a board featuring nearly 10 types of tater tots, hit Blue Rooster Food Company in the Old Port.

With so many fantastic options, dinner is where things get complicated. Start with a late-afternoon snack of a dozen Maine oysters and a decadent brown butter lobster roll served in a steamed Asian-style bun at Eventide Oyster Co. Sit at the oyster bar and get the celery gimlet to go along with it (have them use Plymouth gin). Trust us. It’s fantastic. For dinner, go early and put your name in at Central Provisions to get an array of oft-changing seasonal sharable plates like semolina cavatelli; tuna crudo from Maine; and crispy fried pork with a kabayaki glaze. While you wait for your table, head up the street to Portland Hunt & Alpine Club for craft cocktails and Scandinavian-inspired bites like gravlox on brown bread with cream cheese and capers. For a bit more upscale yet hardly fussy meal, get a reservation at Street & Co. (or its harder-to-get-into sister spot, Fore Street). Start with the chicken liver mousse and the beautiful grilled octopus with Maine potatoes, then move on to scallops pan-seared in Pernod. End up at Novare Res Bier Café to find a deep selection of craft beer from Maine and around the world as well as a focused spirits and wine list.

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Ram Island Lighthouse in Portland, ME
Ram Island Lighthouse in Portland, ME Inbound Horizons / Shutterstock


This is a water town—and it requires you to get out. Check out Portland Paddle to rent kayaks and stand-up paddleboards. You can venture out on Casco Bay solo to visit the numerous islands or sign up for a guided tour. While the water may be chilly, you can rent surfboards and take lessons at Maine Surfers Union. Walk through Munjoy Hill to hit the Eastern Promenade and hike along its 2.1-mile waterfront trail with mouth-dropping views. Or pick from more than 70 miles of Portland trails to keep you active whether walking, running, or biking, including a 45-mile forested trail system in nearby Falmouth. Fancy yourself a fisherman? Sign up for a lobstering excursion with Lucky Catch Cruises. Take a trip up to Freeport and sign up for one of L.L.Bean’s Outdoor Discovery School Adventures to learn how to fly cast, kayak, paddleboard, shoot archery, and more.

Then there’s the beer. With about 20 around town, Portland has one brewery for nearly every 4,000 residents, so pretty much anywhere you go, you’re not far from a fresh pint. Go old school and head to Allagash Brewing Company, where you should get a tall glass of the Allagash House Beer, great for a hot day and only available at the brewery. Allagash offers $5 hour-long tours daily that include a guided tasting of four beers. The hottest brewery in Portland right now is Bissell Brothers. So get in line (usually wrapping snake-like around the block) to score a few cans of their flagship, The Substance or their double IPA, Swish—both as rare and sought-after brews as you’ll find in the craft beer world.

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