Maine is one of the prettiest states in the U.S. Full stop. It’s one of the few destinations in America where unspoiled wilderness is still a guarantee, as well as with a historic New England charm to be found in its seaside towns, lighthouses and rocky beaches. But while its biggest city, Portland, is relatively compact by the standards of nearby metropolises like Boston—or even New Haven, which has twice its population—it’s a charming and cosmopolitan city with a unique character all its own.
Just a few hours’ drive from Boston or an hour by plane from New York City, Portland is a modern city that wears its history on its cobblestone streets. A fishing town with the aesthetics of old New England, it’s picturesque with lots to explore, from its seaside attractions and museums, numerous breweries and boutique shopping to its culinary scene, which is growing into one of the best in the country right now. Here’s where to go in Portland.
Where to Go
True to its name, Portland is a port city with a long history of commercial fishing, as well as being the second most active port by tonnage on the eastern seaboard. Naturally, the Old Port neighborhood is one of its biggest draws, though not because of its catch. Paved with cobblestones and lined with boutique shops, restaurants and breweries, Old Port is a quaint and scenic part of the city to visit with no particular agenda in mind, other than to catch a glimpse of the historic side of Portland while taking advantage of its nightlife and shopping.
To see the weirder side of Maine, duck into the International Cryptozoology Museum, which chronicles the strange and mysterious world of cryptids. A sizable portion of the museum is dedicated to Sasquatch, but the creature features run the gamut from a life-sized coelacanth model to P.T. Barnum’s FeeJee Mermaid (which was a hoax) and lore about the Mothman. Whether or not its exhibits make you a believer, it’s a fascinating compilation of curious sightings and the folklore that keep the legends alive.
For a different kind of Strange Maine, head up to Congress Street to pay a visit to the namesake record shop mostly stocked with used gems. In fact, in the span of just a single block, you’ll encounter a number of worthwhile record haunts, including Electric Buddhas and Moody Lords, the latter of which is a vintage shop notable for its well-curated selection of vinyl, from rock and jazz to krautrock and Afrobeat. But if it’s fashion that catches your eye rather than racks of records, visit Material Objects for a funky selection of vintage and consignment items to peruse.
For those seeking more of an active outdoors experience, head to Fort Williams Park, just a 15-minute drive southeast of downtown Portland. A 90-acre park overlooking Casco Bay, the landmark is a mixture of green space and historic ruins, featuring batteries formerly in use by the U.S. Army in the early 1900s and the Goddard Mansion, former home to Civil War Colonel John Goddard. Visitors can walk along the cliffside, cool off at the rocky beach, visit the children’s garden or pick up a snack at one of its handful of food vendors. Speaking of which…
Where to Eat
When in Maine, lobster rolls are a must, and Portland has ample options for those who crave buttery fresh catch in a fluffy baked roll. Formerly a food truck, Highroller offers full-sized rolls or a flight of three smaller rolls with your choice from 15 different sauces, including jalapeño mayo, curried ketchup, lobster ghee and Old Bay. For those seeking more diverse lobster experiences, however, they also have lobster mac and cheese, grilled cheese, BLT and the Surf and Turf: a burger topped with lobster. With two locations, including a truck at Fort Williams Park to sate the appetite of coastal hikers, Bite Into Maine draws long lines for its many varieties of lobster rolls, including wasabi, chipotle, curry and Maine style (mayo and chives). There’s no reason to stop after just two, however, and Portland Lobster Company, Luke’s Lobster and Eventide Oyster Company are all worthwhile places to get your fix.
For breakfast, you could probably still find more lobster if you wanted to (and why wouldn’t you want to?), though the best way to start your day is with a sweet and indulgent donut. The Holy Donut opened in 2010, offering a unique spin on an A.M. treat with their own recipe that utilizes riced potato, adding a richness in texture and flavor to their donuts—which include flavors such as blueberry cinnamon sugar, dark chocolate coconut and honey lavender. Hifi Donuts also offers its own rich and flavorful “old-world” style donuts in decidedly new world flavors, like salted double chocolate, the Simpsons (pink frosting with sprinkles) or the Portland Fog: bergamot and lavender blended with cream.
The stylish, yet unpretentious, Sur Lie is an example of how on-point Portland’s culinary game is right now, earning two James Beard nominations this year for Best Hospitality and Outstanding Restaurateur for owner Krista Cole (who also owns Gather). Both of which are well-earned—the service is top notch, and its tapas-style menu is rife with standout dishes. Among its highlights are the rich and creamy crab dip, the herbed popover (with lobster, of course!), and its creative cocktail offerings, which include non-alcoholic offerings.
Housed in a 150-year-old brick storehouse on the waterfront (moved from a prior location and rebuilt brick by brick), Twelve is an aesthetically exquisite dinner destination with a prix fixe menu of fine-dining offerings including Atlantic cod in carrot bisque, or a tender ribeye with black garlic. An a la carte menu is also available, featuring entrees as well as snack items like chips and dip (trout roe optional), but whichever menu experience you choose, make sure to get the fresh baked rolls, which are as savory and craveable as anything else on the menu. Twelve also has a stellar cocktail menu featuring both updates on classics like an Aperol spritz or unique creations such as the Bait and Switch, featuring vodka, Aperol, bell pepper, pineapple and allspice. It’s worth it to stop by here just for the cocktails, though there’s a number of other great watering holes in Portland worth a visit as well.
Where to Drink
Blyth and Burrows is a must-visit for cocktail drinkers as well as those who enjoy a dozen oysters on ice at happy hour. Sophisticated yet lively, the Old Port bar features maritime furnishings like brass diving helmets and mounted ships’ figureheads, while the menu is stacked with innovative signature cocktails that come in several different varieties: clarified (milk punches, etc.), stirred, shaken and carbonated—the latter of which also comes bottled for at-home enjoyment. Their update on the mai tai, Seabeast Takes a Lover, might not immediately feel like being whisked away to the tropics (Maine’s a bit too far north for that), but it’s milk-clarified mixture of rum, orgeat, curacao and lime is still paradise in a glass.
A colorful dive bar with an idiosyncratic, scrappy character, Bubba’s Sulky Lounge is popular with tourists and locals alike, but the vibe is decidedly more low-key than Blyth and Burrows. Often packed with a younger crowd on weekends, its quirky decor—big on taxidermy—is immediately charming. Come dancing on a Saturday night, or simply pop in early for a frosty pilsner.
Portland is also home to a long list of breweries well worth visiting, including Allagash, Austin Street and Lone Pine. Alternately, Maps is one of the city’s best beer bars, an intimate basement brewpub featuring a regularly changing tap list of both local and international beers, as well as a vast collection of vinyl for spinning in-house to help complete the vibe. They also serve cupcakes, if you’re seeking something sweet with your suds.
Where to Stay
Lodging in Portland comprises a wide range of options, from the quirky and youth oriented Black Elephant Hostel to the luxurious Blind Tiger. For a stay that sits somewhere between the two, check out Cambria Hotel, which opened in 2021. It’s a preferable option for those seeking a comfortable and bright environment with modern furnishings, and it also has pet-friendly rooms for those traveling with a furry companion. The rooms are spacious and quiet, and depending on which side of the building you’re staying on, offer city or bay views. Located in the Old Port part of the city, it’s also conveniently located just blocks from city attractions, and the lobby is usually stocked with fresh baked cookies for guests.
Jeff Terich is a Richmond, Virginia-based freelance writer whose work has appeared in SPIN, Bandcamp Daily, uDiscover Music, Grammy.com and San Diego Magazine. His Twitter is @1000TimesJeff.