Weekender to Portland

What's new in this historic port town just two hours from the North Shore.



Looking for a great weekend escape? Consider Portland, Maine, which keeps upping its cool quotient. Beyond its historic architecture and bustling seaport, it has world-class arts, including its own ballet, opera, symphony, theater, and museums like the Portland Art Museum. It has tempting boutiques on crooked back streets, oodles of standout restaurants, and several old neighborhoods becoming so lumberjack chic that some locals now refer to their city as “Portlynn.”   

 Two great places to stay include The Danforth Inn and The Press Hotel. The former is a luxury inn about 20 minutes by foot to the waterfront district and set in an 1823 brick building, but with a glamorous, modern, interior—think cobalt velvet sofas in the dining area, a faux moss hanging light near the lobby and pops of colors throughout—purple pillows, green glass sinks, and hot pink suede stools. The hotel has a sweet little bar, which makes excellent cocktails, and an elegant Southeast Asian restaurant, Tempo Dulu, where chef Michael MacDonnell offers such dishes as tamarind-glazed foie gras, Malaysian-style lobster tail, and spicy roasted duck with chile-garlic jus. All rooms have different stylish interiors and most have working fireplaces. Steps from hotel, you’ll find Victoria Mansion (also known as the Morse-Libby House), a national historic landmark and considered one of the most important historic homes of the 19th century in the country. You tour this beautifully preserved home to see the intricate plasterwork and woodwork, exquisite furnishings (like the double pink and gold bowl sinks), and most of the original wall paintings, many trompe l’oeil, by the Italian-born artist Giuseppe Guidicini.

The Press Hotel, formerly the Portland Herald Press headquarters, opened in 2015. In a nod to the building's previous use, the hotel has playful newsroom references throughout—rugs with scattered letters on them, quips in unexpected places, and clever art installations, like the one in the main lobby composed of a mass of vintage typewriters. The 110 rooms channel 1920’s writer’s offices, each one with a vintage-styled journalist desk, but with modern comforts like flat-screen HD television; bathrooms with rain shower heads; and Frette linens. In addition to Inkwell bar and café, the hotel has Union restaurant, where you can simply savor a cocktail at the marble bar or enjoy an elegant Maine-inspired meal—braised lobster with fall vegetables.

One of Portland’s latest hotspots is Thompson’s Point. It’s located on a nose of land jutting into the Fore River in northwest Portland that previously was an industrial rail-yard. Although plans for future restaurants, shops, and a hotel are in the works, current businesses include Cellardoor Winery at the Point, where you can sample more than 20-plus wines at a dramatically long bar or buy bottles to go in the adjoining shop. Next door, you’ll find Stroudwater Distillery, which serves cocktails fabricated from their corn-based vodka, gin, and bourbon and rye whiskey—also available as shots. Neighboring Bissell Brothers Brewery offers tastes of their different beers, which are only available in Maine. For sustenance, there’s Big J’s Chicken Shack serving crunchy, golden buttermilk-brined fried chicken, as is, in sandwiches or over waffles.

For something novel to see on Thompson’s Point, stop into the world’s only International Cryptozoology Museum, which explores the world of hidden and unknown animals, like Yetis, Bigfoot, and sea serpents, along with recently-discovered creatures, like the okapi, which looks like a zebra wearing a brown sweater on its torso and is related to the giraffe. At Circus Maine, a circus school, you can watch performers train through the tall glass windows or take a class yourself!

Another area to explore is Portland’s East End, known for its gorgeous Eastern Promenade, a 2-plus mile paved walking, jogging, and biking path that hugs the water. In the residential Munjoy Hill area, running along Washington Avenue, several funky spots have recently open, including Drifter’s Wife wine bar. Former Brooklyn residents, Peter and Orenda Hale, opened this tiny eatery in the front of their wine shop, Maine & Loire, which specializes in organic, chemical-free wines. Enjoy those wines at the bar and or with whatever Peter Hale is cooking that day—perhaps lamb with lentils, yogurt, and sesame. Across the street, Izakaya Minato, channels Tokyo through plates of pristine sushi and Japanese bar food, like miso-marinated mackerel, and okonomiyaki (savory Japanese pancake), and kimchi fried rice.

Other excellent restaurants worth visiting include Eventide Oyster Co. and its sister eatery next door, The Honey Paw, which opened in 2015. Eventide, which opened a smaller outpost in Boston’s Fenway Park area this October 7, has bountiful raw bar options, buns with fried oysters, fish sandwiches, and burgers for meat-lovers. The latter specializes in creative Asian dishes, such as Vietnamese crepe with maple-sweetened fish sauce and smoked lamb with curried egg noodles. Over in the Old Port area, Central Provisions offers unusual wines with umami-rich small plates in a casual, wooden table setting. Look for dishes like the whole artichoke with lobster aioli; fried cauliflower buds with crispy chickpeas and feta; and suckling pig with apples and brown butter. Down on the waterfront Sam Hayward (of Fore Street fame) has opened Scales to serve off-the-boat fish and seafood simply prepared: mussels steamed in hard cider; grilled whole sea bream with chimichurri; and fried fish of the day with sweet and sour vinaigrette.

On par with Portland’s incredible food scene, is the city’s craft beer movement. To date, Portland has 20-plus breweries with more opening all the time. You can explore these breweries on various tours, or follow the Maine Beer Trail, “a guide to Maine’s Best Breweries,” which includes all the breweries in the greater Portland area.    

For shoppers, the city has all kinds of stores, ranging from touristy outposts along the wharf area to unique boutiques, such as those along Exchange Street in the Old Port area. As for museums, the Portland Museum of Art warrants a peek. The museum has more than 18,000 works in its collection, ranging from Andy Warhol and Winslow Homer to Renoir and Jasper Johns. Child’s Play: Representations of Adolescence in America through photographs runs until December 17, Nan Golden, which explores the body of work the photographer, runs until December 31, and Model Citizens: Art and Identity in the United States runs until January 28, 2018.  Next door is Children’s Museum & Theater of Maine, which has all sorts of interactive exhibits, including the Farmer’s Market, which teaches tots math skills as they learn about Maine’s local food movement.

From the North Shore, it takes approximately two hours by car to get to Portland, which makes it a very manageable day trip. But given all there is to see, do, taste, and explore, consider staying for longer.  

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