There’s something undeniably alluring about Portland, Maine. Maybe it’s the scent of evergreens in the salty air. Or, the quaint cobblestone streets that lead to the historic wharves. Or, the endless array of hip shops, candle-lit restaurants, and lively bars. Whatever it is, Portland, Maine is filled with charm—the kind that captures your heart and keeps you wanting more.
Though the city is Maine’s most populous, it retains an appealing small-town vibe. Perched on a coastline of pure beauty, its sandy coves and rocky shorelines offer secret summer escapes without the crowds, while downtown, the art galleries, antique shops, and beer gardens are bustling with activity. It truly is the best of all worlds—whether you’re looking to enjoy the last quiet moments of summer on the beach, set sail on crystalline waters, or explore a new seaside scene.
Not to mention: Some truly exceptional eats. Along with sampling the outstanding dishes from an outstanding array of restaurants, cafes, and coffee shops, the chances of scoring the freshest lobster roll you’ve ever had are very high in Portland—especially since approximately 90% of the entire country’s supply of lobster is sourced from Maine. For the best place to find the lobster roll of your dreams—as well as tips on where to stay and what to do—read on.
Where to Stay
Portland newest indie hotel opened in 2024 and is already garnering accolades thanks to its sleek design by award-winning firm Post Company. Named after the poet Henry Wadsworth Longfellow—a Maine native—the West End hotel’s 48 guest rooms, restaurant, lobby bar, and spa draw inspiration from the “wild, untamed beauty of the New England coast” as well as the city’s distinctive historic charm. Think: moldings, ceiling medallions, granite, and wide-plank wood floors as well as artwork and artwork from local artists and makers. At the hotel’s restaurant, Twinflower Cafe, you’ll find healthy breakfast and lunch fare, while lobby lounge Five of Club offers classic cocktails, craft beers, and small bites in an modern-meets-old school salon-like setting. But the hotel’s real gem? Astraea Spa, which features a full roster of treatments as well as a sauna and meditation lounge.
Nestled a few blocks from downtown Portland, Blind Tiger offers nine unique guest rooms housed in a mansion built back in 1823. From the spacious suites outfitted in an effortlessly cool aesthetic that still feels warm to the lounges adorned with refined vintage furniture and modern art accents, every room is proof that age is just a number. Unlike traditional hotels that can feel too tired or trying, Blind Tiger embodies cozy and chic with ease. After raiding the pantry stocked with gourmet snacks galore, don’t forget to check out the former speakeasy turned billiard room for a round of pool.
A multi-story floor to ceiling wall stacked with typewriters welcomes guests to the Press Hotel. Once the Portland Herald Press headquarters, the hotel elegantly embeds its journalism history with contemporary and clever twists. Below the lobby, a permanent gallery featuring local Maine artists is a must-see, as is the fully stocked state of the art gym ready for a sweat session on the go. Perhaps the most centrally located hotel in Portland, the Press Hotel is a few steps from just about everything. While the walls are literally inked with wit and wisdom from the past, the hotel is writing a new story rooted in exemplary service and style.
With views of Crescent Beach from every corner and the ocean’s omnipresent scent, Inn by the Sea lives up to its name. Located just 15 minutes from Portland, the pet-friendly resort offers vacationers an idealistic Maine escape with the convenience of exploring both the city and coast. All 61 suites are dressed in playful nautical decors like antique buoys, but still feel sophisticated enough for a longer stay—and are equipped with everything you’d need to do so, from unlimited coffee to lobster crackers. Beyond the spa, heated swimming pool, and lavish outdoor lounge areas, a picturesque boardwalk guides guests through a sea of local wildflowers out to the beach, which is outfitted in matching blue umbrellas and chairs. Surprise summer treats like s’mores, bonfires before sunset, and ice cream socials fit for kids and adults alike make days spent at the Inn that much sweeter.
Where to Eat
Sister restaurant to Portland’s iconic Fore Street, Scales serves upscale seafood in an understated, stylish setting on the wharf. The knowledgeable staff is eager to make the local fare fit every craving. While halibut dressed in a buttery hazelnut sauce will change your life, the freshest oysters from across the state are also an absolute must.
Once a highly sought-after food cart stationed at local haunts, The Highroller Lobster Company eventually found a permanent home in the heart of Portland a few years back. Today, there is still a line down the street to order one of the many creative takes on the city’s claim to fame, a lobster roll. Try the gooey lobster grilled cheese or the crispy lobster taco.
At this globally-inspired New England small plates dining destination, chef Mimi Weissenborn serves up locally-sourced ingredients, fresh-caught seafood, fine wines, and craft cocktails in a vibrantly-hued, plant-filled space. Sample it all by opting for the tasting menu, or take your pick of dishes like spruce-smoked Maine sea scallops and Gulf of Maine mussels in coconut curry broth from the a la menu.
Run by James Beard award-winning restaurateurs, the Honey Paw serves an eclectic menu focused on South East Asian cuisine. Try the khao soi with smoked lamb, and their take on a Banh mi (made with chicken liver mousse for the carnivores, tofu for vegetarians). Every Honey Paw meal should be finished with a soft-serve swirl—the flavors rotate seasonally.
At this Brooklyn-inspired deli, you’ll find some of the city’s best bagels, lox, pastrami sandwiches, and fresh-baked rye. Step through the red-brick facade any morning of the week for a coffee and a nosh—and don’t miss out on the latkes served with applesauce and sour cream or the matzo ball soup. On Sundays, they even offer a special, Maine-inspired schmear: blueberry cream cheese.
For a sweet treat and a stellar cup of coffee, don’t miss Tandem Bakery in East Bayside. Housed in an adorable 1930’s building and run by husband-and-wife duo Will and Kathleen Pratt, Tandem offers house-roasted, single-origin brews and seasonal blends alongside the most delectable biscuits and morning buns baked by James Beard nominee Briana Holt. Just one note: Wi-fi isn’t available—but there are plenty of places to read and chat. They also offer a curated selection of vinyl records for sale. “The space was designed with the intent of making it feel like you are stepping into a home, a place where strangers quickly become friends,” the Pratts say on their website. (Note: Tandem also has another location housed in a former gas station and laundry mat on Congress Street in the city’s West End that follows the same analog plan.)
Situated in the center of Old Port, Via Vecchia’s ivy-laden facade opens up to a sultry cocktail bar that sparkles with its array of gold shakers and stirrers. The elegant entrance makes you think for a second that you might actually be in Manhattan. The outdoor patio is ideal for a sceney night while the expansive indoor space is best suited for a romantic supper. Via Vecchia’s Italian spin on classic cocktails steals the show and pairs well with their refined pizzettes and pasta dishes.
Terlingua is a Texas barbecue escape serving everything from smoked brisket to spicy chili in the East End. The multi-level outdoor space is hangout friendly for a drink from the lengthy mezcal menu leading into a full meal. Vegetarians will still find something to love with esquites and the corn, bean and mushroom frito tacos.
Where to Drink
Blyth Burrows is more than a cocktail bar dressed to the nines; it’s an immersive sensory experience. If you’re lucky to sneak into the back bar hidden behind a bookshelf, try one of the New England Clambake cocktails created to put a summer party in your mouth. Also make note of the dollar oyster deal every Wednesday.
Maine Beer Company does more than IPAs and pilsners. Located a few miles north of Portland, the sleek company headquarters houses multiple tasting rooms and serves up an artisanal selection of wood-fired pizzas. Sometimes the best meal is as simple as a pie and pint!
Marked with a vibrant mural off Washington Avenue, Oxbow is a buzzy brewery and beer garden. The East End hotspot serves fermented farmhouse ales, cold brew flights, and fruity rosés to boot. Onsite is an outpost of Duckfat, which offers Portland’s famous fries that are, yes, fried in duck fat. A perfect pick me up during days spent sipping cold ones.
What to Do
Located in downtown Portland, Judith is a retail beacon among a plethora of bustling restaurants and bars. The contemporary concept store carries a global collection of ready-to-wear lines including Batsheva, Maryam Nassir Zadeh, Henrik Vibskov, Baserange, Rachel Comey, and Ulla Johnson. Beyond clothes, the minimalist-minded store sells natural beauty products and modern home goods.
One of Maine’s most iconic landmarks, the Portland Head Lighthouse rests at the edge of Cape Elizabeth s rocky shoreline in Fort Williams Park. Walking trails along the coastline are lined with goldenrod and blueberry bushes; they lead directly to the lighthouse s entrance at the tip of the cove. Situated just 15 minutes south of the city, the lighthouse is worth the short journey for the breathtaking views and a buttery lobster roll from Bite into Maine.
Take a spin in the shoes of local lobstermen on a cruise through Casco Bay. The hands-on tour offers guests the opportunity to catch their own dinner and learn about all things lobsters. Aboard a lobstering boat aptly named Lucky Catch, check on traps positioned around Portland s harbor. Don t fret about getting your clothes wet: the crew outfits everyone in rubber gloves and gaiters to stay dry (and clean!).
The Portland Museum of Art features rolling exhibitions from renowned artists in addition to mainstays like Claude Monet and Henri Matisse. Make your way through the multi-floor museum’s spacious galleries filled with natural light before winding into the McLellan House and the outdoor sculptural park. Located at the top of Congress Street, the museum is central to coffee shops and cocktail bars for an àpres-art drink.
Covering the eastern corner of the city, the sprawling promenade features 180-degree views of Casco Bay. Watch boats and barges head into the harbor while enjoying a picnic on the grassy lawn. Local food trucks like Mr. Tuna and Totally Awesome Vegan Food Truck serve up everything from fresh sushi to jackfruit pastrami sandwiches. If the water is calling your name, there are paddle boards, kayaks, and more ready to rent.
Perched on the Fore River, Thompson’s Point hosts a music series in the summer before transforming into an ice-skating rink throughout the long winter. Either season, make sure to grab a pint at Bissel Brothers brewery or a stiff one at Stroudwater distillery while exploring Portland s West End.
Located a stone’s throw from the Portland Museum of Art, this historic Art Deco theater features Moorish-inspired architectural details, decorative columns, and vaulted ceilings—in fact, you could say it’s a work of art in its own right. After falling into disrepair—and a few decades as an “adult” theater—it was purchased by New York’s The Bowery Presents and extensively renovated into an intimate concert venue. In recent years, it’s hosted national acts ranging from Elvis Costello to Iron Wine to The Flaming Lips to MGMT to Aziz Ansari—so it’s definitely worth checking the roster of upcoming events if you happen to be in town and in the mood for a show.
