What to Do in Portland, ME

When Brooklyn transplants Peter and Orenda Hale first opened their natural-wine shop, Maine & Loire, “we’d uncork bottles and ask our friends and neighbors 
to come over,” recalls Orenda. “But it wasn’t enough. We wanted a real spot where like-minded people could eat and drink.” So over the winter the Hales built Drifters Wife, a wine bar, in the front portion of the 
store. The rotating menu of simple dishes, such as bread with warm La Tur cheese and olive oil, is by chef Ben Jackson, another former Brooklynite. Drifters Wife feels 
like it could be in Williamsburg (which is appropriate since the couple met working at Reynard at the Wythe Hotel). “Everyone thinks a wine bar is cheese and charcuterie, and that’s chill,” says Peter. “But where we’re from, it’s about the vibe.” 63 Washington Ave. drifterswife.com.


Texas is nearly 2,000 miles from Maine, but it doesn’t seem all that far when you’re eating barbecue at this white brick house on Portland’s newly buzzy Washington Avenue. Owner Pliny Reynolds and chef Wilson Rothschild focus on Mexican 
and Southwestern smoked meats, including a salt-cured pork belly chicharrón, 
slow-cooked over local applewood and paired with Portland beers, like those 
from Austin Street Brewery. Reynolds even commissioned a Maine-born artist living 
in Texas to create the logo. “We’re not trying to be a big, old-school Texas barbecue place,” he says. “We just want to bring the communal spirit of barbecue to Maine—getting together with friends and watching the football game and drinking beers.” 
52 Washington Ave. terlingua.me.


“A lot of people say, ‘I never would’ve thought of this,’” says Jason Loring, owner of this underground tiki bar. “But it’s a no-brainer. A tiki bar is definitely something Portland needed.” Loring envisioned Rhum as a place to wait out Maine’s long winters, but large-format cocktails, massive seafood towers and tropical drinks (served in tiki mugs made by two local Portland artisans) are ideal for summer. Look for the semi-hidden entrance, where a wood ramp leads to a blacked-out cavern with a giant octopus painted on the windows—“Indiana Jones Temple of Doom–style,” Loring says. 4 Free St. rhumportland.com. 


Genoan chef Paolo Laboa gets credit for teaching Danny Bowien of NYC’s wildly popular Mission Chinese the tricks to 
an award-winning pesto. Laboa is now bringing his native Ligurian food to a brick-lined space on Commercial Street, where waiters wearing patterned shirts and crisp denim aprons deliver boards 
of traditional thin-baked foccacia. Our favorite dish? The famous pesto, of course, on handkerchief pasta. 100 Commercial St. soloitalianorestaurant.com.


It’s easy to miss this to-go window behind 
a coffee shop, where Natalie “Figgy” DiBenedetto dishes up cast-iron fried chicken and biscuits inspired by her childhood in Missouri. “It felt like fried chicken was one of the final food trends 
to reach Portland,” she says. “I could 
do it blindfolded.” The signature Ay Ay Ron, 
a cheddar biscuit piled high with chicken, buttermilk mashed potatoes, slaw and gravy, is almost too large for one person to finish. “It’s either really big guys or the tiniest women who order it,” DiBenedetto says. “Then they devour every bite.” 
 722B Congress St. figgystakeoutandcatering.com.


What do you do when you find an abandoned rail yard in Portland? You turn it into a multipurpose food destination. The newly launched marketplace features 
a distillery, a winery and the local Bissell Brothers Brewing Co. Come to drink, eat fried chicken at Big J’s or take in an outdoor concert featuring headliners like The Lumineers and Leon Bridges. thompsonspointmaine.com. 


Chef David Levi of Portland’s hyper-local Vinland explores his northern Italian heritage at this natural-wine bar on tiny Bramhall Square. Start with a spritzer 
at one of the small tables out front (the potted herbs are those they use behind 
the bar) before stepping inside for mussels in white wine or spaghetti in squid ink. 
3 Deering Ave. rossobianco.me. 


Some of the best pastries and coffee in town are at this retro gas station, where vintage lettering that reads brakes and shocks still remains above the neon bakery sign. Owners Kathleen and William Pratt have created a laid-back, all-day hangout (there are now two Tandems in town). Baker Briana Holt turns out brilliant cookies and pies as well as “loaded biscuits” spread with butter and housemade jam in flavors like strawberry tea flower. In the evenings, look for beer-based cocktails and pop-up collaborations with local chefs. 742 Congress St. tandemcoffee.com/bakery. 


This long-awaited reopening is the hottest seafood restaurant in the city, courtesy 
of Sam Hayward and Dana Street of revered Fore Street. Located on the refurbished Maine Wharf, it evokes iconic New England with steamers and an exceptional warm lobster roll, plus reimagined classics like cod with brown butter. “When you’re on the ocean, the first thing you want to do is open the windows,” Street says—and every table has a view of lobstermen hauling their catch onto the docks. 68 Commercial St. scalesrestaurant.com.


“We call it a nondenominational noodle bar,” says Mike Wiley, who co-owns The Honey Paw with Andrew Taylor. “It gives 
us the freedom to do whatever the hell 
we want.” At this next-door neighbor to 
the pair’s superpopular Eventide Oyster Co., chef Thomas Pisha-Duffly explores the noodle spectrum, from pig-head tortellini to smoked lamb khao soi. Everything’s served on mismatched china; framed menus from Chinese buffets 
and a wraparound wall of booze add to 
the eclectic, kitschy feel. 78 Middle St. thehoneypaw.com.


The style is modern maritime: Walls are covered with navy blue stripes, lights swing from knotted ropes and an outsize photo of a lobster boat battling stormy 
seas sets the mood. But this isn’t a seafood joint. Chef Anders Tallberg’s food is Italian-American: leafy Caesar salads, big bowls 
of creamy Bolognese. Cocktails are also 
a highlight, with drinks like the Equinox, made with gin, lemon and Maine 
berry preserves. 59 Washington Ave. roustabout.me.


Housed in what were once the offices of the Portland Press Herald, The Press Hotel takes stylistic cues from its history: Hallways are decorated with memorable news headlines (“Elderly lobster set free”), and 
a massive scale, once used for weighing paper, sits in the gym. Borrow one of the hotel’s 12 bikes, equipped with coolers, for a picnic on nearby Cape Elizabeth, or eat at Union, where native Maine chef Josh Berry cooks with local ingredients 
in an open kitchen. 119 Exchange St. thepresshotel.com. 


At this 1700s farmhouse not far from Ogunquit’s picturesque Nubble Light, 
ex–Wall Street financier Ben Goldman has created a self-sustaining restaurant: 
A “micro farm” supplies sorrel and radishes for dishes like Little Gem lettuce 
with sunflower tahini; beehives provide honeycomb for the outstanding cheese 
and homemade charcuterie plates; and 
a backyard orchard grows the heirloom apples that go into the shrubs. Goldman encourages guests to wander the grounds before sitting down to dishes like roast pork shoulder with garlic scapes. “Grab a glass of Riesling at the bar,” he invites, “and go exploring.” 37 Ogunquit Rd., Ogunquit. thevelveteenhabit.com.


Biddeford—18 miles south of Portland—is a derelict mill town in the midst of a rebirth. Travelers are coming to eat at the revived 1920s Palace Diner and to tuck into small dishes at Custom Deluxe. Owners Thomas Malz and Meghan McVey describe the place as a working-class bistro, serving simple New England farm food with a Quebecois twist. Roast chicken thighs come with buttered sticky rice, mushroom aioli, pea sprouts and poached egg, 
and smoked pork belly is served with fingerling potatoes, yogurt and dill. “We’re trying to evolve into the most boot-stomping, mud-slinging, North-country restaurant we can be,” says Malz. 140 Main St., Biddeford; 207-494-7110.