Portland, Maine is a terrific destination for a weekend getaway (a one-hour flight from New York City) or a night respite when driving up from the city to points north. While the city’s small downtown area can’t shake its sad, seedy, empty-storefront vibe, the Old Port, with its working harbor, eatery-packed piers, cobblestoned streets and brick warehouses repurposed as restaurants, breweries, and retail shops, holds history and charm. For New Yorkers, Portland may be the closest city (if you can call it that, with a population of just under 70,000) to feel very far away.
Much has been written about Portland’s food scene, which boasts more excellent restaurants than you might imagine, with a number owned by former big-city chefs drawn to Maine’s natural beauty, slower pace of life (granted, running a restaurant anywhere is stressful), and easy access to high quality locally sourced provisions. Most – but not all – of these restaurants are in neighborhoods away from the Old Port, particularly in Portland’s picturesque East End.
Ask a food-savvy Portlander where the locals eat and, especially at the height of the tourist season, you may hear “at home.” True, in summer the Old Port can be overrun with cruise ship passengers combing Commercial Street gift shops for lobster-themed swag. But locals do eat out, all four seasons of the year. Here, I offer you a walking tour (a car works, too) of some of my favorites and others I hear good things about in Portland’s East End.
MIDDLE STREET
Walk east along Middle Street, two streets up from the harbor, just beyond the Franklin Street Arterial, and you’ll get to a small oasis of eateries that includes – at the very end – my favorite Portland Japanese restaurant, Benkay.

(Photo by Carolyn Swartz)
Benkay Japanese Restaurant and Sushi Bar
So you live in New York City, a sushi capital of the world. Why seek it out in Portland? Because Head Chef Hiro Isshi, who initially came to Maine from Japan to work in the sea urchin (uni) industry, serves an astonishing and ever-changing variety of fresh, highest quality fish sourced locally from the Gulf of Maine and flown in overnight from (e.g.) Japan, Canada, and Spain.
Behind the sushi bar, a blackboard lists new arrivals. (Several had Japanese names I didn’t recognize.) Service here is friendly and helpful, so ask your server to walk you through the choices. Better still – since words and comparisons can’t quite capture tastes and textures – order the omakase, or “chef’s choice ” and let Chef Hiro and his capable crew dazzle you with a stunning, jewel-like collage of the very best they have in house. The vibe is low key; prices are reasonable and fair. You can order your omakase either as sushi or sashimi. (I prefer to see my raw fish naked.) Either way, two of everything make it perfect for “ohmygod, taste this one” sharing.
We started our feast with a flavorful miso soup and bright seaweed salad and rounded it out with one of Hiro’s special maki rolls—not that we’d have walked away hungry if we hadn’t. Of course, Benkay offers a full menu of innovative Japanese appetizers, mains, raw fish options a la carte, salads and desserts. But in a word: omakase. You can thank me later.
Also on Middle Street, with seating indoors and out: Eventide, offering raw shellfish platters and dainty portions of chowder, fish and lobster dishes, and a bit of a wait to get in; Mr. Tuna, for reinvented handroll and other Japanese dishes enhanced—but not overpowered— with the likes of toasted tempura flakes, yuzu spiced mayonnaise; The Honey Paw, a non-denominational Asian-fusion noodle bar with something for every food preference and allergy; East Ender, for salads, wings, burgers, cocktails and brews with a side of Karaoke; Ribollita, a worthy sleeper serving in house-made pasta, seafoods and Italian favorites like risotto and the soup the place is named for; Duck Fat, for specialty sandwiches, milkshakes and Belgian frites; and catty corner on India Street: Dok Mali–tasty Thai street food and dim sum with a popular Happy Hour.

EASTERN PROMENADE
Walking east from the Old Port, Fore Street turns into the Eastern Promenade, a connected series of grassy hillsides, designed by Frederick Law Olmstead, that look out at Casco Bay. At the very top, a pretty panorama opens up of white sailboats and skiffs in an expanse of harbor and a few of the Bay’s 100+ islands. Sit on a bench, stretch out on the grass, or walk down to the half dozen food trucks below, standing nose to tail, like so many circus elephants. We split a lemongrass beef Bahn Mi sandwich, and each ordered a couple of fantastic handrolls from Mr. Tuna (spicy scallop-and-crab is a standout). Then, we indulged in a salted caramel pistachio cup of gelato from Gelato Fiasco.
Other options include tacos, falafel, and sometimes pizza and donuts. While we were eating at a nearby picnic table, a tiny locomotive rumbled past—horn tooting, steam whistle blowing to the delight of kids and families aboard the open cars.
MUNJOY HILL
Across from the Prom is Munjoy Hill, a hilly, historically immigrant neighborhood of worker homes and treelined streets that, following a mid-century decline, has become one of the most desirable parts of the City. Sadly, gentrification comes with the downside of a number of unfortunate teardowns, with viable New Englander homes replaced by faceless, flat-roofed luxury multi-units. Still, for the most part the Hill, as it’s affectionately called, retains its integrity and scrappy vibe.
MUNJOY HILL- CONGRESS STREET
Along Congress Street, which starts at the very top of the Prom, you have a few nice dining options, all with indoor and outdoor seating, just a few blocks away. Check online for days and hours.
The Front Room Restaurant and Bar
This is a long-standing favorite that’s been dishing “upscale” (but never fussy) breakfasts, brunches, lunches, and dinners for over thirty years. The room is unapologetically boisterous, bordering on noisy, with service so friendly it’s practically intimate. We had brunch: tasty Bloody Marys, good coffee and a couple of different benedicts – lobster for him, gnocchi and lardons for her. Sign on the wall: raw oyster special on Wednesday afternoons.
Jing Yan East End Neighborhood Tavern and Low Key Munjoy Hill
On the very next block: an Asian-Fusion (“silk road”) joint with a wood burning oven, cool lighting, and a long zinc bar; and directly across the street, its baby sister, Low Key, serving wildly inventive cocktails, small plates, and soft-serve blueberry ice cream.
Walk two more blocks and you come to Belleville, beloved for flaky laminated dough pastries like sweet and savory croissants, cardamom buns, Kouign-amann (a traditional pastry from Brittany, France), morning buns, in-season fruit tarts, and, later in the day, pizza. Not surprisingly, the owners trained in Paris.
WASHINGTON AVENUE
From here, Congress Street begins its slow descent into town. Halfway down, you’ll come to Washington Avenue, Portland’s newish Restaurant Row. Bang a right – here are the places I know.

Oxbow Blending and Bottling
Portland has, at last count, an almost unbelievable twenty-seven breweries. This one is an urban outpost for Oxbow’s farmhouse brewing, a sylvan campus experience 50 miles north. Here, Oxbow turns out a wide selection of farmhouse ales and lagers of distinctively European influence which can be savored at handcrafted indoor and outdoor bars. Check out the oak barrels and stainless-steel tanks filled with saison (a pale colored ale) and mixed-fermentation wild ales. Hungry? Enjoy your brew in a tucked-away stone patio where a Duckfat outpost dishes up a variety of tasty snacks—including its signature fries. In the evening, there’s live performance: hip-hop, rock, jazz and rock nights hosted by legendary MC’s you may have heard of, but I haven’t.

Sissle and Daughters: Portland Maine Cheesemongers
Even if you don’t have a cooler or fridge at your disposal, don’t miss this world-class cheese (and more) shop where owners Will and Mary Sissle and their knowledgeable staff offer a thoughtfully curated selection of artisanal cheeses and charcuterie, domestic and European, in a welcoming atmosphere that takes the mystery out of getting to know and love quality cheese. Will’s pedigrees from esteemed fromageries on both coasts show in the delightfully varied selection he puts out with care—every cheese at the right time in the right way. If you’re driving out of town (or it’s lunchtime) grab one of the sandwiches made in house throughout the day: great cheese and charcuterie on the Old Port’s fresh Standard Baking James Beard award-winning baguettes. We loved the flavor and crunch of the Parisien, with ham, cheese, house-made pickled red onion, mustard and tender greens; and the satisfying simplicity of the Jambon Beurre: French ham with cultured butter, c’est ça. Browse the pantry shelves for oils, vinegars, mustards, tinned fish, fair trade spices, and reasonably priced wine; and the refrigerator case for burrata, feta, and much more.

The Shop by Island Creek Oysters (Photo Credit: Jamie Curio)
The Shop by Island Creek Oysters
Manager Kip Pascal describes The Shop as the place to get fresh Maine oysters without the wait and formality of a restaurant in the Old Port or downtown. Offering comfortable seating inside and out, The Shop limits its menu to five or six different types of Maine oysters (order as many as you like) and small plates: caviar, deviled eggs, crab roll, and spreads made from fancy tinned fish. If oysters aren’t your thing, tell Kip what is. Washington Ave is a community, he says. And he’ll point you in the right direction.
Terlingua Restaurant and Market
Get better-than-authentic Texas-style BBQ—all rubs, no gooey red sauces —slow-smoked in small batches, daily, in-house. Great guac and chips. We loved the tacos: succulent brisket and juicy pulled pork, one of each for each of us. I’m sure the other menu items, including adobo roasted chicken, fried fish, and oyster mushroom tacos – are just as good. What you can’t see from the unimposing street view: Terlingua has lots of additional seating out back on a pleasant deck and in a spacious, landscaped multi-level garden.
Also on Washington Ave:
Cong Tu Bot: a quirky Cambodian restaurant with a migraine-producing website, brusque, matter-of-fact service and hyper-delicious food that make it all worthwhile; Strata: not food but arguably the best knife/kitchenware/cookware/cookbook shop in New England. The staff here love a good sharp edge and fine handle and will happily walk you through their extensive collection of new and vintage knives, many from Japan. Li’l Chippy: Casual fish and chips, oysters, and sandwiches (fish, crab, mushroom, chicken) for everyone. Kids menu, too. Izakaya Minato: exquisite presentations (the stoneware alone is to die for) of well-prepared Japanese country cooking – cooked and crudo – on small plates that give you the opportunity – and, okay, the need to sample more. Forage Market: if wherever you are, you crave a morning bagels fix, forage’s wood-fired bagels, layered with cream cheese, locally smoked Brown Trading salmon, pickled onion, caper, tomato and greens, do the trick; Onggi: a pint-sized specialty all-things-fermented food shop and bakery, Grab a Miso maple cafe au lait with a sourdough chocolate chip cookies or a kimchi corn soufflé.
THE OLD PORT
Locals do, as I mentioned try to avoid the Old Port in summer, except perhaps to pick up fish for dinner at Harbor Fish on Commercial Wharf, which welcomes visitors just popping in to admire its mind-boggling selection of fish and shellfish in an atmosphere that smells only of clean ocean. For dining out, there are also a few excellent restaurants that locals reserve, in general, for special occasions. If your Portland plans include one or you’d like to create one, none will disappoint.
Fore Street, named for its location, occupies a giant brick warehouse that was once part of a shipyard, with much of the cuisine fired up and roasted in open wood-burning ovens. Under the same ownership, the grotto-like Street and Co. is a “Mediterranean, bistro style, all-seafood restaurant” on a picturesque cobblestoned alley just up from the harbor (leave your heels at home). A few years ago, these two well-seasoned sister restaurants were joined by Scales, a contemporary, luxurious seafood emporium with a stylish indoor space deck seating that looks out at fishing boats in their slips. (Understand, this is a working harbor, not an idyllic seascape.)
A bit off the beaten path at the far (east) end of the harbor is Twelve, run by a team with creds from Per Se, Daniel, and Eleven Madison Park, with a well- appointed dining room adjoining an open kitchen. Expect your server to regale you with detailed descriptions of reductions and infusions of exotic ingredients you’ve never heard. It’s theater for sure—well rehearsed and smoothly delivered—and if the food didn’t measure up (which it does) it would all be a bit much. Evo Kitchen + Bar, an independent Mediterranean and Middle Eastern-inspired restaurant adjacent to (but not part of) the Hyatt. Sit at the horseshoe shaped bar looking out at the kitchen to see how the sausage (and everything else) gets made as food slides in and out of salamanders to shorthand callouts among the staff. (I kept waiting to hear “Yes, Chef” but never did.) Or reserve a table upstairs if you want to see your food only when it’s served to you and ready to eat.
I’m not a fan of diners. But I probably shouldn’t write about the Old Port without a mention of Becky’s Diner, open from early morning to 9 p.m., which is midnight by Portland standards. Here’s where you’re likely to be downing your waffles or chowdah elbow to elbow with real-deal lobster and fisherfolk. I also have it on good authority that Becky’s serves whole-belly fried clams. Watch for that and inquire wherever you’re eating, because whole belly clams are the only kind you ever want to have.
Top photo: Bigstock





