Maine’s Most Famous City Is Actually Better in the Off Season

Portland, Maine easily holds the title of New England’s sweetheart. More than 8 million people flock to this seaside city every summer—that’s more than seven times the population of the entire state, by the way—and there’s a reason this city is a summertime staple for so many. Perhaps I’m stating the obvious, but there’s no better place for a long-weekend getaway fueled by prime seafood, quiet beaches, and nautical vibes aplenty. But as a born-and-raised Mainer, I’ll let you in on a little secret: There’s no bad time to visit my hometown.

To relegate this compact city to one season would be a huge mistake. Spring can be dreary, but there’s some romance in exploring under an umbrella while breathing in the salty air. Fall is a leaf-peeper’s paradise, and Portland makes a stunning homebase as the state shows off its autumnal hues. Even the brutal winter is quite picturesque, as crowds thin out and cobblestone streets lead to cozy pubs filled with locals. So while some seasons are more popular than others, Portland is charming year round. Escape to the all-seasons getaway and see why.

1 hour and 45 minutes from Boston, Massachusetts
5 hours from New York, New York

There’s nothing more synonymous with Maine than lobster. So rather than just crack one open during your time in Portland, learn about the state’s greatest crustacean and get out on the water. The crew at Lucky Catch Cruises typically uses its fleet for commercial fishing, but they invite guests aboard each summer (May through October). After heading out into Casco Bay, take in views of the city and the state’s iconic lighthouse, Portland Head Light. Throughout the 90-minute tour, you’ll pull traps, measure each lobster to follow local protocol while learning about the industry’s sustainability measures, and even get a chance to take home your catch.

Once you’ve learned a thing or two, you’ll appreciate each bite a little more as you get your fill of lobster at local eateries. Find solid, classic rolls at The Highroller Lobster Co. and Bite Into Maine or sample the fancified brown butter lobster roll on a bao bun at Eventide Oyster Co. Just about any seafood spot in town will offer up a whole lobster dinner, but Portland Lobster Company’s outdoor space overlooking the wharf is the most scenic spot to dig in.

The rest of Maine has a leg up on Portland when it comes to outdoor adventure—just look north to Acadia, one of the most popular national parks in the country. But you can still find ways to enjoy the great outdoors on a quick weekend trip.

Maine boasts more than 4,500 islands along its rocky coast, and Portland alone can claim hundreds of them. Some say there are as many islands off the coast of the city as there are days in the year, so the islands that dot Casco Bay are nicknamed the calendar islands.

Make a point to explore at least one of them during your trip. Hop on the ferry and head to the most popular, Peaks Island, where you can rent a bike to get around or peruse the extremely quirky museum dedicated to umbrella covers. Or take a wider tour aboard the Mail Boat Run. You’ll cruise around alongside real mail carriers as they deliver to residents of Little Diamond, Great Diamond, Long, Cliff, and Chebeague Islands.

From curated shops and galleries lining Commercial Street to a small-but-mighty museum, Maine’s artist community makes its mark on the city in numerous ways. Although it’s teeny tiny compared to institutions like the Metropolitan Museum of Art or Boston’s Museum of Fine Arts, the Portland Museum of Art is the oldest public art establishment in the country, first opened as The Portland Society of Art in 1882. Pieces range from international greats like Andy Warhol and Edward Hopper to local legend Winslow Homer—his former studio, located just outside the city in Scarborough, is open to tour.

The first Friday of every month draws makers of all kinds to Congress Street for the First Friday Art Walk, where they showcase their work to the public and offer some goods for sale. Bookmark Creative Portland for intel on other artsy events like shows at the ’20s-era State Theater and an annual printmaking festival.

For a road-trip treat: Each morning in Portland—as the lobstermen come back from fishing and sane people roll over in bed—lines run out the door from bakeries like The Holy Donut, Tandem Coffee + Bakery, and recent James Beard Award-winner ZU Bakery. Each is worth the wait (and the early wake-up call).

To try even more seafood: Lobster may be the grand dame of Maine seafood, but the state has so much more to show off. On the high end, Scales is home to a stellar raw bar and carefully crafted seafood dishes—and its waterfront location means it couldn’t be closer to the boats that bring in the goods every day. Meanwhile, J’s Oyster Bar is an old-school spot to eat a few oysters or fried seafood alongside grizzly local fishermen tossing back martinis.

For a day-drinking session: Portland has the highest number of breweries per capita of any other city in the US. Since stalwarts like Allagash and Shipyard came on the scene in the ’90s, dozens of other craft breweries have popped up exploring just about every style you can imagine. Some of the best taprooms to hang out in include Oxbow Blending and Bottling, Austin Street Brewing, and Bissell Brothers.

To understand the scene: Portland has long been touted as a foodie destination, so hit up the spots that helped it earn that reputation. The upscale eatery Fore Street was among the city’s first buzzy spots, and it remains worthy of your time. Meanwhile, playful Thai fried chicken at Crispy Gai, cocktails with Puerto Rican flare at Papi, and Vietnamese fare at Cong Tu Bot prove the city’s got range. Twelve is perhaps the most ambitious fine dining restaurant in the city at the moment, serving a seasonal prix-fixe menu crafted by Eleven Madison Park alum Colin Wyatt.

For a nightcap: Things tend to quiet down early in this sleepy small city. So if you want to know where the party is after hours, look no further than Room for Improvement. With dive bar vibes, excellent renderings of classic cocktails, and Mind Erasers that give you a chance to brave a sample of local Allen’s Coffee Brandy, this neighborhood favorite is an excellent place to wrap up the night.

For historic luxury: Some of Portland’s most luxurious hotels lean into the city’s storied past. Blind Tiger occupies two townhouses in Portland’s West End neighborhood that date back to 1869. The Press Hotel, housed in the former printing factory for the local paper, is decked out with inky touches and odes to the city’s biggest headlines. And the Portland Regency Hotel & Spa revamped a former 19th-century armory into a cozy retreat with dark woods and rich fabrics.

To stay like a local: Check out The Weldon, a new apartment-like hotel where each room has perks like a full kitchen and in-unit laundry. It’s located a block from the city’s working waterfront, leaving you in the center of the action with amenities that’ll make you feel at home.

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