The Best Things to Do in Portland, Maine
This New England "city" (its population is 67,000 and still is Maine's largest) boasts a small town vibe that has been beloved by its residents for centuries. And they've done a fairly good job at keeping their secret hideout under wraps. But for the last couple of years, city mice from other eastern seaboard towns (NYC, Boston, Providence), have been making their way north to this peninsula in Casco Bay to experience the historic port charm that has become rife with trigger words like “craft beer,” “warehouses,” “foodie,” and “weed.”
Portland epitomizes the deep-Northeastern experience, conjuring visions of fishermen walking streets straight out of an L.L. Bean catalog. That Portland’s still here -- lighthouses, lobster rolls, and plenty of opportunities to use the word “quaint” -- but things are changing. These days, bearded brewmasters seem to outnumber actual fishermen. The food scene has morphed into world-class, destination dining that doesn’t start and stop with lobster. Artists and creatives are flocking to the city’s shores. And word is spreading so fast, it won’t be long before the vibe starts to feel on par with the next, well, Portland. Or Asheville. Or Denver.
I was lucky enough to visit Portland last September, and I have to say I fell head over heels in love. So much so that I’d actually consider moving there if not for the 9-month-long winters. That said, as soon as it’s safe to travel, you can bet that we’ll be renting a car and driving up to experience more of this charming, coastal city. (But, please, do not travel yet. Just file this away for when it’s legit safe to hit the road.)
Here are my picks for the best things to do in Portland, Maine.
The Best Time to Visit Portland
Not right now, obviously. This is all hypothetical for when travel reopens because, and I can’t stress this enough, you SHOULD NOT BE TRAVELING RIGHT NOW. But I digress..
If you like cozying up with scarves, mittens, a toasty fireplace, and a lot of snow, Portland certainly delivers in the fall and winter -- and spring, honestly -- when you'll also be tempted to leave the city for skiing. If you’re coming to Portland to experience its rich maritime culture, you’re going to want to stick to the warmer months. Portland summers, though short and sweet, are sunny, warm, and come with lots of activity on the water -- aim for July or August.
The Best Things to Do in Portland, Maine: Day 1
Arrive at Portland's International Jetport, just 2 miles from downtown Portland, then head downtown. The Portland, Maine hotels in the heart of the city are key, given its smaller scale and easy walkability. For quick access to the sheer volume of restaurants, galleries, shopping, and 'grammable #content, you're going to want Old Port. This is the heart of Portland's history, from the brick facades and cobblestone streets, to the working waterfront, along with a range of quality hotels and nearby Airbnb options that will keep you tapped into the main vein.
Grab a decadent lunch at James Beard-nominated Central Provisions -- don't skip the bone-marrow toast -- then wander around Old Port and downtown to get a feel for the colonial coolness (it's a thing) of the city. In the evening you'll want to visit The North Point, which has fantastic cocktails and globe-spanning meat and cheese boards in a brick-laden, cozy atmosphere.
The Best Things to Do in Portland, Maine: Day 2
If you want to maximize your outdoor time then summer and fall are the best times to visit Portland, Maine. After breakfast, head over to the waterfront to take a trip out onto Casco Bay to explore the many Calendar Islands that scatter across it. (Fun fact: The Calendar Islands got their name from Captain John Smith -- yeah, that John Smith -- because he thought there was an island for every day of the year. Truthfully, there are only 220.) One of Portland residents' most beloved is Peaks Island, just an 18-minute ferry ride from the city. Cycle through the country lanes to look at the colorful cottages, sprawl on the pebbled beaches, or eat fantastic lobster rolls at The Inn on Peaks Island.
When you head back to the mainland, pop by the iconic Holy Donut for one of their classics (these are potato donuts made with all-natural ingredients, if that somehow makes you feel less guilty).
The Best Things to Do in Portland, Maine: Day 3
Full disclosure: I am not a beer person, unless it’s a light Mexican beer on a hot, sunny beach. But you’d be foolish to come to Portland and skip its breweries, even if just for the atmosphere, some great food, and a social vibe. Portland's brewery scene is one of the fastest growing in the country. I will say you're doing it wrong if you don't take advantage of food trucks and pale ales at Rising Tide Brewing; farmhouse ales at Oxbow Brewing Company; ever-changing canned New England IPAs and crisp pilsners at the white-hot Bissell Brothers; and legendary Belgian-style beers from Portland OG Allagash.
Most of the breweries have good food options, but this is also a good day to stop in at Duckfat: A stalwart of the chef-driven sandwich movement and a can't-miss bite in the city. They serve up sandwiches like the next-level Overnight Duck Confit with duck fat-fried frites and donuts. Which is to say, it's good, rich beer-crawl food.
Pro tip: If you’re a wine-lover (much like myself), then Cellardoor Winery at The Point is an absolute must. This lavish tasting room is opulent, but cozy, with twinkling chandeliers, sumptuous couches, and an entire wall of wines. While Maine isn’t one of the great wine regions of the world, this was definitely a highlight for me.
The Best Things to Do in Portland, Maine: Day 4
If you like history and culture, you will probably want to snap a picture of the Portland Head Light. It's the oldest lighthouse in Maine, and one of the most photographed. Grab an Uber out to Fort Williams Park to check it out up close, along with the namesake fort, a historic mansion, and more. It's not an entire day's worth of an activity, but it is a cool photo op. Back in the city, there are plenty of museums and galleries to check out, like the Portland Museum of Art, which has its fair share of Warhols and Monets.
In the evening make your way over to lovely West End, which is known for its quiet waterfront park promenade, as well as its explosive sunset views. Come dinner time, head over to Washington Avenue, an emerging neighborhood that is being highly praised for its burgeoning restaurant scene. Here is where you'll find everything from a fresh raw bar at The Shop by Island Creek Oysters to El Salvadorian cuisine at Tu Casa.
After dinner, dip into some speakeasy culture at Blyth & Burrows for a strong, mixology-driven cocktail, plus more oysters and a toast to a city that has now become one of your favorites.
The Best Things to Do in Portland, Maine: Day 5
Make one final eating stop at Bayside American Cafe for a legendary brunch -- think smoked salmon platters, lobster Benedict (one of six Benedicts available), and strawberry cheesecake French toast -- before hopping on your flight back to wherever it is you came from.
Portland, Maine Hotels:
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Portland Maine Pro Tips
Stay in Old Port, especially if you’re a first timer.
Make a day on the bay. Go sailing out on Casco Bay, explore the Calendar Islands, eat all the lobster rolls.
Portland, Maine’s restaurants are world-class. You should eat in as many of them as possible.
Don’t skip the nature. Maine has some rugged, raw, and wild scenery and getting out into it should be top priority.