Why Portland, Maine, Is the New Portlandia

Surprise! Portland, Maine, is just as happening as hipster haven Portland, Oregon. (Photo: iStock)

For a couple of years, my boyfriend, Dan, and I had been talking about our desire to visit Portland, Maine. Beautiful bucolic beaches, authentic salt-of-the-earth people, and great lobster rolls (did I mention I really love lobster rolls?). Plus, Dan has a group of colleagues who live there.

When I read my friend and favorite author Kate Christensen’s new book How to Cook a Moose, about moving to Portland, Maine, I was even more inspired. Kate’s book is a fun and smart culinary memoir and something of a love letter to this coastal New England city. She left Brooklyn to live in Maine, which makes sense because Portland is like the new Brooklyn, if Brooklyn were occupied by a white-haired army in L.L.Bean puffy coats.

But don’t take that as a crack on Portland’s authenticity. This town is practically built on grit, with a history that includes several bombings and four fires, one in 1866 that destroyed most of the commercial buildings, half the churches, and hundreds of homes and left 10,000 people homeless. Rebuilding is what they do here.

It’s also inevitable to compare this Portland to Fred Armisen and Carrie Brownstein’s Portlandia because, well, the name is the same. And while there are definitely similarities to Portland, Oregon (localness is next to godliness), it is smaller and truly New Englandy, and at 9 p.m. on a Saturday night nary a store is open.

Related: City Smackdown: Portland vs. Portland (Oregon and Maine, that is)

Portland’s latest rework has blended its marine heritage with a decided artistic twist. This newer Portland is heavily influenced by the arrival in the 1990s of the Maine College of Art. This brought students from all over the world and the kind of things artsy kids want and need: live music, artisanal coffee, and those sort of Smurfy-looking hand-knit beanies.

The weekend we arrived was a “leaf peeper” weekend, when hordes of out-of-towners come to gape at the foliage. To quote my mother, “I don’t get it. If you’re driving somewhere and you see some nice fall trees, you say, “Hmm, nice tree — but to make a vacation out of it?”

Nonetheless we were there for it, and I will say the leaves were dynamite.

The Press Hotel, which used to be home to a printing press. (Photo: The Press Hotel)

The Press Hotel was a perfect place to stay, in a building that formerly held the printing press for the Portland Press Herald. The décor is an homage to all things font and type (the back of the chair in our room said “The quick brown fox jumps over the lazy dog”). What struck me most were the people at the hotel: Everyone was so nice, and not fake nice. The valet earnestly told us about how he angled our rental car so we wouldn’t have to stress about the bumper of the car in front of us.

Everyone recommended we eat at Eventide, a highly regarded restaurant known for its incredible oysters and seafood. Dan’s friend had said, “Go, and if it’s crowded … I guess wait for a table.” I said, “Well, do they not take reservations?” And he thought for a moment and said, “I guess they do.” Portland people would just as soon wait than get hung up on reservations. Alas, Eventide was too crowded. So we met Dan’s colleagues for cocktails at Portland Hunt and Alpine Club.

Related: The Perfect Coastal Maine Road Trip

Then it was on to dinner at the Union restaurant at the Press Hotel, which had plenty of local fish and more of those incredibly nice people. When I tried to order a side of potatoes with my lobster and gnocchi, the server gently suggested that unless I was carb-loading, it might be overkill, but she did bring me a huge basket of local fresh bread just in case my blood sugar dipped.

The Porthole, a former dive bar. (Photo: The Porthole Restaurant/Facebook)

The next day, we met Kate and her practically-husband Brendan at the Porthole, a local establishment. Apparently, it used to be a true dive, with bilge water on the floor and rats playing poker at the other tables, but the Board of Health shut it down. Now it has reopened in A+ sparkling style. We sat outside because it was one of those last sunny, warmish fall days. Fishing boats came in as we drank very good $2 beer in giant plastic cups and ate delicious lobster rolls and fish tacos in purple shells with beet salad.

Kate, who is a true gourmet, also likes to gives back and has cooked fine cuisine for a local homeless shelter. She said the people of Portland take amazing care of their homeless, to the point that it has become somewhat of a destination for the homeless. After lunch we passed a guy who was asking for spare change and wearing crisp layers of flannel and performance fleece.

The atmospheric Portland Head Light. (Photo: Raging Wire/Flickr)

That afternoon, we went to Portland Head Light, the most photographed lighthouse in the U.S. You can see why: It is very photogenic. We strolled on the rocky beaches of Kettle Cove and took plenty of Instagrams of glittery water and seaweed.

Related: Secret Maine Beaches You Need to Know About

Kate, who is gluten free, had recommended Vinland for dinner. If you’re an organic, gluten-free, local-food-loving person, this is your Lutèce. Instead of olive oil there’s housemade ghee. Thankfully, the wine was not local. But my Iowa farm boy was in a bit of a panic when he realized a gluten-free restaurant probably doesn’t give you a big ol’ basket of Parker House rolls. Every time he took a bite of his dinner, he said, “I think this is might be an acorn.” Our server was saddened to tell us that they’d run out of the night’s special, pig jowls. (I don’t eat any pig, but my hope was that pig jowls came from a pig who felt his face was too fat and was having work done.)

Worshiping the mighty doughnut at the Holy Donut. (Photo: The Holy Donut/Facebook)

You can’t go to Portland without a quick stop at the Holy Donut (insert Homer Simpson noise), which sells artisanal flavors like maple bacon and dark chocolate with sea salt. My favorites were the ginger sugared variety, which tasted like apple cider doughnuts. Of course, there was also a large supply of gluten-free.

We couldn’t leave Portland without a quick zip over to the outlets of Freeport, Maine (about a 20-minute drive). Dan was crying and moaning, because he’s not a shopper.

I didn’t want anything except a light fleece jacket for my daughter. It had to be black (“to match her soul”) and hooded. I went into Patagonia (more nice people), but the prices were very Patagonia-ish. I’m from the land of people who believe outlet prices should be $12. Not $260 reduced to $220.

I ended up getting her a jacket in the L.L.Bean not-outlet store because the only fleece hoodies in the L.L.Bean outlet were Kermit the Frog green, more Elmo than Emo.

During the trip — which was maybe 18 minutes — Dan texted me from the car 15,000 times that he was sorry we had to break up, and that he’d gnawed off his leg. Thankfully the reception was terrible so I didn’t get most of the messages.

I allowed him a small reward of a coffee on the way out of town. The very nice guy who was making his Americano was about to move New York to be a barista and a poet. He was actually going to be living in Jersey City. “You know,” he said in perfect Maine earnest, “it’s the new Brooklyn.” Hmm, you don’t say.

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