By Robin Catalano
Even on a raw, rainy afternoon, with a uniform blanket of cinder-block gray settling over the sky, it’s easy to see why Portland, Maine, has smitten so many travelers. Raindrops the size of lima beans melt down the sides of buildings. The wind whooshes and gusts, cutting through coat sleeves and tossing hats. Atlantic waves wallop the jagged rocks in a spray of white foam. Still, the city seems just as beautiful, and possibly even more transfixing, as it does when there are blue skies for miles over Casco Bay.
From native son Henry Wadsworth Longfellow to naturalist-philosopher Henry David Thoreau and professional travel curmudgeon Bill Bryson, this coastal city has inspired rapturous recollections among writers. This is in part because it has been a scenic and strategic port for nearly 200 years (it celebrates its bicentennial in 2020). But the onetime capital of Maine is also a genius of reinvention, having been reborn five times following mass fires.
The first was in 1775, during the Revolutionary War, when British Navy Captain Henry Mowat gave the city’s residents two hours to evacuate before pounding the downtown with artillery. (A cannonball from the attack is still embedded in the chandelier of the First Parish Church on Commercial Street.)
The most significant was on July 4, 1866, when an errant Independence Day firecracker set off a blazing chain reaction, razing 1,800 homes and commercial properties and leaving 10,000 homeless—and toughing it out in tents all the way through a bitter New England winter. Surveying the ruin, Wadsworth wrote, “Desolation! Desolation! Desolation! It reminds me of Pompeii.”
Each time, Portland has risen like a phoenix from the ashes; it’s no accident the mythical creature is one of the city’s symbols. During the past century, it has invented itself again, this time as a hip, laid-back, artsy-foodie coastal city—not as weird as its West Coast sister, much more accessible and less people-packed than Boston, and more scenic than a city of skyscrapers like New York.
With an open-minded population of 65,000, postcard-worthy coastlines and cobblestone streets, a walkable downtown with a plethora of independent businesses, and more restaurants per capita than any other U.S. city, Portland has topped a number of best-of lists, including National Geographic’s Best Small Cities in the U.S. and BonAppétit’s Restaurant City of the Year. Whether you live in the Northeastern United States or are visiting a variety of locations around New England, Portland is a happy-making bite-size getaway for even the most jaded traveler.
Here’s how to spend 48 hours in Portland.
Day 1 in Portland
The most helpful way to get to know the city is with a historical lay of the land, courtesy of one of its many tour companies. Top choices include the Real Portland Tour, where you’ll be shuttled to significant points of interest downtown and along the coast by a lifelong Mainer; Historic Workouts, led by a fitness instructor and history buff, which will help you burn calories while seeing the sights; and the Portland Fire Engine Co., which will transport you from point to point atop a decommissioned fire engine. Or if craft beverages are high on your agenda, skip straight to the Maine Brew Bus, which hits all sorts of grape- and grain-based hot spots.
After your tour, plan to hoof it. Starting in Monument Square, smack-dab in the historic center of town, ogle the many beautiful brick Federalist buildings. Most, which now house shops, galleries, offices, and banks, were constructed after the Great Fire of 1866, and include two dates on their facades: the original construction, and the date of rebuilding. Here you’ll also find the Wadsworth-Longfellow House, the poet’s former home, now a museum run by the Maine Historical Society. Just a few doors down is the sleek, modern Portland Public Library, a fun stop for any literature lover. (Fun fact: the large stone drama mask, now displayed on Temple Street, was once part of the Elm Theatre, which stood on the site where the library is located.)
Heading east, you’ll pass the Post Office, with seven stones embedded in the park out front, representing the islands of Casco Bay. Points on the Portland Freedom Trail, a self-guided tour that documents important locations during abolition, also run through this part of the city.
Stop at regal Portland City Hall, designed by Carrere and Hastings (of New York City Public Library fame), for a photo op on the stone steps, then continue down Congress Street to the Portland Observatory. Built in 1807 and rising 86 feet high, it was once a crucial signal tower for merchants on the bay. Nowadays, it offers some of the best views of the city and the ocean beyond. It’s open only in the late spring through fall, and the hours are sometimes irregular, so check their website before venturing out.
Once you’ve had your morning fill of historic architecture, start the hunt for lunch. There are dozens of options, most reliably good, and some excellent. The hardest part is choosing among them. (See sidebar for some suggestions.)
Stop in most restaurants, and you’ll quickly discover that Maine is serious about its lobster. The state catches 130 million pounds of the crustacean per year, and serves it up in everything from classic Maine-style lobster rolls (served cold, with mayonnaise and spices) to chowders, casseroles, and a modern, dumpling-like take served with brown butter at Eventide Oyster Co.
Follow up with a detour at The Holy Donut, the holy grail of potato-based sweets. You read that correctly: Holy Donuts are made with potato. Crumbly and soft, these cake-style treats have more pronounced and distinctive flavors than most gourmet doughnuts.
After lunch, hit the shops. Save for franchises like Urban Outfitters, most are independently owned and offer all manner of interesting gifts (for you or others), from high-end pet supplies to local cheeses and handmade jewelry.
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Head down to the Old Port for a stop at Harbor Fish Market, where you can choose your catch of the day from selections just off the nearby docks, plus some from farther afield. Next door, take a stroll through Sea Bags, which has been making totes, cosmetic cases, and home goods from recycled sailcloth since 1999. The best part: you can watch the textile alchemy happen in their sewing studio, the backside of which is open to viewing. If you’re extra lucky, you’ll spy harbor seals playing around the nearby Maine State Pier or Ocean Gateway Terminal.
Walk about a half mile uptown to the Arts District, where many of Portland’s creatives work and meet. This is also where you’ll find the Maine College of Art, a five-floor vertical campus housed in an old department store building, as well as a variety of other unusual shops and galleries.
When dinnertime rolls around, you’ll have another painful choice to make on restaurants. Stick around afterward for a nightcap and some live music (Port City Blue is a great choice for the latter). With its dozens of breweries, distilleries, and speakeasies, Portland proudly thumbs its nose at its Prohibitionist past, and offers some terrific craft beverage choices. The city also loves a festival, and whether mainstream or niche, doesn’t seem to miss an opportunity to put one on in the warmer months.
Day 2 in Portland
Get a jump on the day with a cultural attraction or two. The Portland Museum of Art boasts a large collection of exhibitions in American, European, and contemporary art, as well as works by local artists. It’s one of the city’s more popular venues, so expect a crowd.
For a road-less-traveled experience, head around the corner to Victoria Mansion. Built circa 1858 and also known as the Morse-Libby Mansion, it’s one of those “summer houses” built by the well-heeled (in this case, the creatively named hotelier Ruggles Sylvester Morse and his wife, Olive) that dominate the landscape in coastal cities.
Use left and right arrows to enjoy the slideshow below.
Portland’s only brownstone, Victoria Mansion was modeled after an Italian villa, and is strikingly beautiful from the outside. But just beyond the stately, arched front door is where the real treasure lies. From the trompe l’oiel paintings on the walls and ceilings to elaborate gilding and plasterwork, period gas lamps, brilliant stained glass, and 90 percent of its original furniture, Victoria Mansion appears almost exactly as it did in its pre–Civil War splendor. It’s also the only intact example of the work of interior designer Gustave Herter, who was one of the most influential designers in the late mid-to-late 1800s.
For a road-way-less traveled experience, skip the traditional cultural touchstones and travel northwest to the International Cryptozoology Museum. Filled with sasquatches, abominable snowmen, sea monsters, and other what-the-holy-hell? interpretations of creatures that may or may not have existed (nice to meet you, fur-bearing trout!), the museum may not persuade you that these beasts are alive, but it’s worth a detour to revel in the eccentricity.
Now that you’ve seen some of Portland’s many indoor attractions, it’s time to take it outside. Affix your jaw firmly back in place as you drive along Cape Elizabeth; there’s even more scenic coastline to come. Craggier than an old farmer’s face and full of dramatic cliffside sweeps and swirling inlets and coves, it’s the stuff of outdoor-recreation legend. You can’t go wrong stopping at any of the beaches that dot the coast, but top choices include Scarborough, with its views of the elegant, and sometimes enormous, estates beyond; next-door Ferry Beach; and smaller but no less charming Crescent Beach.
Among Portland’s most memorable outdoor attractions are its many lighthouses, built in a variety of styles and dating back to the 1700s, to offer safe passage along Maine’s ship-gobbling coast. Several allow free climbs to the top during Maine Open Lighthouse Day on September 14, but even if you’re not in town that day, they’re worth touring from the outside.
Heading from Ferry Beach back toward the downtown, your first stop should be Two Lights State Park, named for its—wait for it—twin lighthouses. The eastern light, Cape Elizabeth Light, is still in operation, while the western was decommissioned and privately sold in the 1950s to eccentric actor Gary Merrill (formerly Mr. Bette Davis), who sold it in 1983.
For a taste of unadulterated Maine seafood goodness, don’t miss the Lobster Shack at Two Lights, located right at the rugged edge of the park, overlooking panoramic views of the Atlantic. A family business for the past half century, the Lobster Shack doesn’t do froufrou. Instead, you’ll find a menu of classic lobster, clam, and crab rolls, plus fried-fish plates and chowder, many at affordable prices.
Continue on to Portland Head Light. George Washington commissioned it in 1787, but it wasn’t completed until 1791. Eighty feet high and more than 100 feet above the water, this iconic beacon is said to be one of the most-photographed lighthouses in the world. It’s also been the site of many heartbreaks, including the 1886 wreck of the Annie C. Maguire, a British barque that struck the coast while sailing from Argentina to its home in Quebec. Everyone aboard made it safely to shore, but a rock on the south side of the lighthouse has been painted with the commemorative date.
On a clear day, from here you can also see Ram Island Ledge Lighthouse, located in Casco Bay on a slim strip of rock, to mark the northern entrance of Portland’s outer harbor.
Stop for a snack refueling at The Cookie Jar, a favorite among locals for doughnuts, apple pastries, and lobster-shaped shortbread cookies. Then drive on to the campus of Southern Maine Community College, where you’ll find the parking lot for Portland Breakwater Lighthouse, or Bug Light, as it’s known locally for its diminutive size. (The Spring Point Inn, also located on campus, is one of the best-kept secrets for lodging in Portland, especially in the more affordable shoulder seasons.) Watch your step over the unevenly spaced stones leading up to the lighthouse, and pause at the end for incredible views of Casco Bay and Fort Gorges, a never-quite-finished military fort that on foggy days seems to hover over the water.
If you’ve had quite enough of looking at the sea and would rather be on it, hop a ferry to tour Casco Bay’s islands. Peaks Island, the closest of the bunch, is a short 20 minutes away.
Among the seven islands, there are 70 miles of walking and biking trails—a nature mecca for the outdoor inclined.
As sunlight fades, the sky over the bay unfolds in a spectacular display of bubblegum pink, azure, and tangerine. It’s as if Portland is undergoing yet another transformation, reminding you that the city will be reborn again in the morning, just in time for another round of exploration.
For more inspiration for where to stay, eat, and shop, plus sites to visit, see the drop-downs below. Portland has dozens of options in each category; this is just a sampling of what we recommend. All opinions are our own.