How to Spend an Excellent Weekend in Portland, Maine
A powerhouse dining scene, hiking trails, and even a cryptid museum call from this quirky city by the sea.
Willard Beach in South Portland, Maine. / Photo by Cynthia Farr-Weinfeld via Getty Images
Portland packs a boatload of personality into one small city. And the perfect part? A go-with-the-flow vibe that’s ideal for weekends that mash up outdoorsy adventure with lazy grazes through the stellar restaurant scene—all fueled by fresh-roasted espresso and local brews. From wood-roasted coffee to a cryptid museum, here’s how to peruse the best that Boston’s neighbor to the north has to offer, under two hours away.
This guide was originally published in August 2023; stay tuned for periodic updates.
START THE DAY
A Holy Donut doughnut. / Photo by Rachel Leah Blumenthal
What’s that magical fried-dough smell that has passersby floating through the air like characters from an old Looney Tunes cartoon? The scratch-made beauties at the Holy Donut, each with a slightly denser texture than your average doughnut, thanks to riced potato added to the dough. Find a rotating selection of around 20 flavors, from classic vanilla to a Maine blueberry glazed donut filled with cannoli cream. There are savory options, too, like bacon cheddar—and yes, they’re delicious. You’ll likely see a line out the door at the Commercial Street location, but head over to the petite Park Avenue spot and you’ll be in and out in no time.
Revving up for a day of sightseeing is easy, thanks to indie coffee shops on basically every corner, like two locations of the delightful Tandem Coffee Roasters. Or if you want to try something different, head to Speckled Ax for coffee made with beans roasted using local wood, which imparts a slightly smoky flavor.
The Holy Donut, 194 Park Ave., Portland, Maine, 207-874-7774; 177 Commercial St., Portland, Maine, 207-331-5655; theholydonut.com.
Tandem Coffee and Bakery, 742 Congress St., Portland, Maine; Tandem Coffee Roasters, 122 Anderson St., Portland, Maine; 207-760-4440, tandemcoffee.com.
Speckled Ax, 567 Congress St., Portland, Maine, 207-660-3333, speckledax.com.
EAT
Eventide Oyster Co. / Photo by Zack Bowen
There’s so much to savor in Portland that you can (and absolutely should) plan a themed weekend around scarfing down as much excellent cuisine from the city’s top restaurants as you can. Feast on lobster stew and oysters at Eventide Oyster Co., the big sister to the Best of Boston Fenway location. Set sail with dinner at DiMillo’s on the Water—a seafood-starring spot in an old ship that’s (you guessed it) right on the water. And celebrate modern New England cuisine at buzzy Twelve, which opened in summer 2022.
Other exciting newcomers offer a chance to globetrot beyond New England. Take Regards, which whisks diners away with Los Angeles-inspired street eats and small bites, including grilled octopus and bluefin toro. The star might be the house-made masa—dough used for tamales, tostadas, and tortillas—which is fairly uncommon in Portland. Consider yourself lucky that Southwest-chic Lenora is open all day, serving breakfast sandwiches and morning guava and cheese pastries, plus all-day eats of tacos, tostadas, and tortas. The inventive shrimp cocktail, meanwhile, puts the chilled shellfish in a clamato broth with chunks of celery, cucumber, and avocado. Served with tortilla chips and saltines, it’s basically an edible bloody mary. Papi transports Puerto Rico to the Old Port, with a concise menu that includes handheld bites of bear-hug flavors—like, say, a bountiful beef empanada. And for dinner, Bar Futo is a feast of Japanese grilled bites and an expansive sake menu. Standouts include the chicken meatballs slathered in garlic soy sauce and the generous chicken katsu with charred onion mayo. Do save room for the kakigori—an instantly Instagrammable dessert that’s a mountain of shaved iced flavored by rotating syrups and toppings.
Eventide Oyster Co., 86 Middle St., Portland, Maine, 207-774-8538, eventideoysterco.com/portland.
DiMillo’s on the Water, 25 Long Wharf, Portland, Maine, 207-772-2216, dimillos.com.
Twelve, 15 Thames St., Portland, Maine, 207-910-7400, twelvemaine.com.
Regards, 547 Congress St., Portland, Maine, 207-747-5940, regardsmaine.com.
Leonora, 2 Portland Sq., Portland, Maine, 207-536-0423, lenoramaine.com.
Papi, 18 Exchange St., Portland, Maine, 207-808-8008, papiportland.com.
Bar Futo, 425 Fore St., Portland, Maine, 207-956-7373, eatfuto.com.
SHOP
Because you can’t possibly go on vacation without buying a T-shirt, hit up the small-but-mighty Maine Souvenir Shop. Rather than a kitsch factory of hackneyed designs, the shop works with local artisans to emblazon their artworks on apparel and more—like the Pigeons Run on Dunkin’ (same) shirt by Flyn Costello.
Continue the quirkiness with a stop at Coast City Comics & the Fun Box Monster Emporium for new and vintage comic books, graphic novels, and statement T-shirts. Come with plenty of quarters to feed the vintage pinball machines and arcade games, too. And don’t be surprised if you leave with treasures to start a “Let me relive my ’90s childhood fantasies” toy collection (where’d your folks put your Super Soaker, anyway?). For reading that leans more novel than graphic novel, visit Longfellow Books to browse some 30,000 tomes. Or, bring a bagful of books to sell to Green Hand Book Shop—but call first, as they sometimes put book-buying on hold. You’re only selling to make more room on your shelf for selections from the shop’s hand-curated used books, anyway.
The Maine Souvenir Shop, 2 Exchange St., Portland, Maine, themainesouvenirshop.com.
Coast City Comics & the Fun Box Monster Emporium, 634 Congress St., Portland, Maine, 207-899-1505, coastcitycomics.com.
Longfellow Books, 1 Monument St. Path, Portland, Maine, 207-772-4045, longfellowbooks.com.
Green Hand Book Shop, 661 Congress St., Portland, Maine, 207-253-6808, greenhandbookshop.com.
PLAY
Allagash Brewing Company. / Photo by Rachel Leah Blumenthal
No need to drive the nearly three hours to Acadia National Park, right outside of Bar Harbor, for hiking trails. Mackworth Island State Park—just an 11-minute drive from downtown Portland—offers an easy and flat 1.5-mile path that circles the whole tiny island, offering plenty of birdwatching. True, Back Cove Trail is more of a walk than a hike, with a 3.6-mile gravel-covered pathway boasting both water and city views. But the parking lot and perfect location right in the city make it a popular spot. Up for a challenge? The Bri-Mar trailhead awaits a 45-minute drive away in Raymond, with a moderately difficult 2.6-mile hike up Rattlesnake Mountain. The sweeping vistas are definitely worth hoofing it up the wooded trails. Before you leave, be sure to grab a to-go order from Po’ Boys & Pickles for a trailside lunch of mountainous sandwiches. If a lazy sunshine soak is more your speed, hit up family-friendly Willard Beach in neighboring South Portland.
Sure, “Keep Portland Weird” might be a slogan for Portland, Oregon, but it basically pertains to the Pine Tree State city, too. Embrace the oddities at the International Cryptozoology Museum, a small museum showcasing exhibits on cryptids—unknown animals—that range from the pop-culture familiar (like Bigfoot) to the more obscure. You’ll also find information about more recently discovered oddballs in the animal kingdom, including a life-sized model of the ancient coelacanth fish. Afterwards, wander the Old Port neighborhood, where you can peek at gorgeous brick former warehouse buildings that see new life as boutiques and eateries. And while it’s downright impossible to pick a favorite brewery among the city’s many options (which only means more weekend trips), do hit up progressive Bissell Brothers and make a pilgrimage to Allagash Brewing Company’s crown jewel of a taproom.
Mackworth Island State Park, Andrews Avenue off US-1, Falmouth, Maine, falmouthme.org.
Back Cove Trail, Portland, Maine, trails.org.
Rattlesnake Mountain via Bri-Mar Trail, Mountain Rd., Raymond, Maine, alltrails.com.
Po’ Boys & Pickles, 1124 Forest Ave., Portland, Maine, 207-518-9735, poboysandpickles.com.
Willard Beach, South Portland, Maine, southportland.org.
International Cryptozoology Museum, 32 Resurgam Pl., Portland, Maine, cryptozoologymuseum.com.
Bissell Brothers, 38 Resurgam Pl., Portland, Maine, 207-808-8258, bissellbrothers.com.
Allagash Brewing Company, 50 Industrial Way, Portland, Maine, 800-330-5385, allagash.com.
STAY
A room at Blind Tiger’s Danforth Street location. / Photo by Read McKendree
Do yourself a favor and skip the big hotels in favor of slumbering in a slice of history. The two guesthouses by Massachusetts-based Lark Hotels—collectively known as Blind Tiger Portland and both located in the quiet residential West End neighborhood—are like twin love letters to the city.
Blind Tiger on Danforth opened in 2020, transforming a former Federalist-style mansion into a design-forward nine-key boutique hotel inspired by the home’s speakeasy past. In spring 2023, Blind Tiger on Carleton first opened the doors to an 1869 row house, reborn as a six-room boutique B&B that brims with original details like historic moldings and fireplaces. The guesthouse is a mix of the social and secluded. The six individually designed rooms—light or dark colorways with décor curated by local tastemakers, king beds, and walk-in showers—offer bubbles of silence to unwind. (Aiding that, the rooms at Carleton Street don’t offer televisions, so save the binge-watching for home.)
The two living rooms on the first floor offer a chance to mix up your own cocktail in the bar area (check out the gorgeous historic wallpaper) and unwind with other guests, or tuck into an art book on the couch. Be sure to snag some snacks from the guest pantry, and get your fill at the feast-like breakfast toast bar. The English garden is the perfect spot to sip coffee as you plan a day of exploring, with everything just a quick walk away.
Blind Tiger Portland, 163 Danforth St. and 46 Carleton St., Portland, Maine, 207-879-8755, larkhotels.com/hotels/blind-tiger.
GETTING THERE
The good: Portland is an easy straight-shot up I-95, which can take around 90 minutes if you’re lucky. The less good: Expect to spend closer to two hours if there’s traffic. But a big silver lining is that the drive cuts right through Portsmouth, New Hampshire, if you want to savor some grub at the city’s excellent restaurants. Plus, you might have to accidentally stop at the Kittery outlets for some retail therapy.
