It had been over eight years since my last adventure in Maine, which involved a car, many hours on the road listening to compact discs (how old am I?), and a magical place called Ogunquit, a seaside town known for its meandering beach walk along the rocks. When I think of Maine, I picture myself there, gazing at the water, inhaling the calm, salty air as my hair poetically dances in the wind. You know what they say about expectations.

I landed in Portland, Maine, late at night. My wet and sticky backpack, courtesy of a fellow traveler’s unannounced spill on the plane, dangled off my wrist. My taxi driver unceremoniously dumped me at my lodging. As I wrestled my suitcase out of the trunk, I was grumpy and sticky and tired, and the only piece of writing my hair was dancing to was Alexander and the Terrible, Horrible, No Good, Very Bad Day. The Inn at Park Spring was warm and inviting, though, and I went to sleep reassured that tomorrow would be better.

Inn At Park Spring
Jet-lagged and bleary-eyed, I made my way downstairs during breakfast hours. I was greeted by John, the innkeeper, whose smile and charm thawed my grumpy soul. He poured me coffee and brought me fresh fruit, gluten-free English muffins, and eggs over easy. The oppressive rain emojis that had appeared in my weather app a week before had grown smiles and transformed into sunshine, and it was time to explore the town.

Old Port
Bam Bam Bakery, a gluten-free joint, was on my radar, and it was only a ten-minute walk east toward the water. Sunlight streamed through the windows and landed on the cases filled with éclairs, cupcakes, and other goodies.
A three-tiered stand stacked high with jam thumbprint cookies and sugar cookies caught my attention, and, though I was still full from breakfast, I bought a sprinkled sugar cookie for future happiness. Old Port is a great neighborhood to stroll, and I popped in and out of shops on Commercial Street.

I wandered farther down to Maine State Pier to check out the water and found myself at the ferry terminal. On a whim, I inquired at the window about a ticket to Peaks Island. Five serendipitous minutes later, I was boarding a ferry bound for this popular destination away from the urban sounds of Portland but only a three-mile trip from downtown.

Peaks Island
After disembarking, I found a shaded bench overlooking the water to eat the sugar cookie I had stowed away. Golf carts and bicycles are the preferred methods of touring if you want to circle the entire island. I opted to grab a coffee from Peaks Cafe and meander up the street and around the corner. As I continued on Island Avenue, a little sign announced “Umbrella Cover Museum.” Inside, a small woman with a giant personality welcomed me into her quirky world of carefully curated umbrella covers. Director Nancy Hoffman’s mission statement is about appreciating the mundane in everyday life, finding wonder and beauty in the simplest of things, and knowing there is always a story behind the cover. I was thoroughly delighted when she pulled an accordion out of the ethers and proceeded to croon a song about letting a smile be your umbrella.

After a quick goodbye, I hightailed it to the ferry and back to the city. The evening was cooling down, and I started to worry I might be cold on the lobster boat excursion I had booked—what a good excuse to souvenir shop! But I had very limited time before I needed to be at the pier. As the writer Paulo Coelho once said, “When you want something, all the universe conspires in helping you to achieve it.” Fate intervened when I walked into Cool As A Moose and found an insanely soft sweatshirt with “Maine” emblazoned across the chest. Sure, Coelho may have been speaking about life purpose, but I’d like to think he also cares about my body temperature and comfort whilst on a lobster boat.

Lucky Catch Cruises
Hoping to catch a bit of golden hour, I had chosen the Whitehead Passage cruise, which took off from the pier at 5:30 and wrapped up around 7:00. Captain Tom and his two crewmates educated us on lobstering rules, like immediately releasing a female lobster that is berried (carrying eggs). The eggs appear as tiny black circles on the underside of the lobster, and a nine-pound female could carry up to 100,000 of them. It is also illegal to keep a lobster that is undersized or oversized, and the lobsters are measured quickly with a double-sided gauge. The tour was chock-full of opportunities to participate, including baiting and releasing the traps and banding the lobster claws once they met all specifications. At several points during the tour, the boat became a bit like a scene from Hitchcock’s The Birds, as the seagulls circled and squawked, attracted to either the fish bait or the smell of tourists who don’t know what they’re doing. At the end of the tour, you could purchase a lobster for a very low price and have it cooked for you across the pier at the Portland Lobster Company restaurant. For the sake of this article, I will pretend I did that and absolutely did not eat french fries at Five Guys.

One Longfellow Square
I’d seen a brochure on the foyer table at the inn about a nonprofit concert venue called One Longfellow Square, and a particular show caught my eye. Luckily for me (and Paulo Coelho, who is quite invested in my trip at this point), the concert was that night. Joe Walsh, a renowned mandolin player, was headlining, and he had brought along a posse of übertalented musician friends. One of them, Berklee College of Music fiddle player Ella Jordan, not only wowed the crowd with her violin skills but also with her voice, which oozed charm, like something out of the 1940s. Sharing the stage with them were Grammy-winning bluegrass guitarist Scott Nygaard and upright bass player Zoe Guigueno of the band Della Mae. The space felt unfussy and warm, and if I lived anywhere near Maine, I’d be a regular here.

Thrift Stores
I’ve been on a mission for years to be friendlier to the environment in various ways—my shower only accepts hipster cleaning goo in the form of bars, my grocery bags are reusable, and I let my produce chill out in my shopping cart without plastic bag cocoons. I also have a great affinity for clothes shopping at thrift stores, and Portland ranks at the top for expertly curated vintage shops. I ended up with pieces from Find, Little Ghost, and Material Objects.

If thrift stores aren’t your thing but you like the idea of shopping locally, retail gallery Maine Craft Portland is the place to go. It’s located in Mechanics’ Hall, a building constructed in 1859 and now on the National Register of Historic Places. The Maine Crafts Association made the decision to lease the first floor of the Hall and renovated it to create this gallery. At one time, the space had housed a jewelry retailer, and the 200-year-old, floor-to-ceiling hardwood-and-glass cabinets have been salvaged and used as a main feature to display wares. Jeffrey Lipton’s pottery made such an impression on me, I checked my suitcase (and my camera!) so I could carry one of his mugs onto the plane.

Empire Chinese Kitchen
When I’m traveling to a new place, I like to star on Google Maps all the restaurants that safely cater to celiac disease, and then I try to find lodging in the densest area of stars. Many years of traveling have taught me I’m willing to walk far distances to get to tourist attractions, but having to walk more than five minutes to find food results in dramatic, hangry meltdowns. Empire Chinese Kitchen was a place I was quite excited about because they have gluten-free dumplings. The waitress recommended the spinach dumplings, as well as the garlic green beans. I know I’m supposed to be talking about lobster, but those spinach dumplings and green beans are still two of the best things I’ve ever eaten.

Harbor Fish Market
As I inhaled my dumplings, a couple at a nearby table suggested I check out the Harbor Fish Market for some good photo opportunities, so I made my way back to the Old Port neighborhood in pursuit of photogenic seafood. A giant tank with live lobsters sat on the left-hand side. A red, metal, vintage-looking scale hung from the ceiling, and buckets of oysters lined another wall, with labels announcing each variety. In the cases were haddock, red grouper, and something called butterfish. An employee smiled at me, and possibly laughed under his breath at the strange woman photographing dead fish. “That’s not a very pretty one,” he suggested helpfully, with a wry smile.

The Promenades
This was perhaps much too ambitious for a hot summer day, but I wanted to be a thorough journalist, so I took myself first to the Eastern Promenade to stroll along the water. I stopped to observe (OK, awkwardly lurk behind) a woman painting en plein air. It was such an iconic artist scene, with her easel and her wide-brimmed hat and her disdain for photographers. I took an Uber to the Western Promenade after treating myself to some pistachio gelato at Gorgeous Gelato. The Western Promenade is a much less populated spot to watch the sunset, and I smiled at two teenagers lying on their backs side by side with their skateboards by their heads. It was so peaceful, the way the sun dipped and filtered through the trees.

This bar is something of an institution when it comes to jazz music, dedicating every Saturday night to it. But I was there on a Thursday, so I watched Zapion and Friends, a group that played Turkish, Arab, and Armenian music. The “friends” part came in the form of a belly dancer with a penchant for audience participation, who gratefully recognized the introverted panic in my eyes and opted to pull a more enthusiastic guest onto the floor. I’m sure Paulo Coelho has some good wisdom for moments like that. I’ll check in with him later.

The Holy Donut
I had one thing on my list before my flight and that was doughnuts—and specifically a place called the Holy Donut that boasts mashed potato doughnuts. I’d gotten the scoop from another inn guest who also had celiac. (I found my people.) She had bought all six flavors of gluten-free doughnuts earlier that morning. I only managed to rein myself in because I was getting on a plane and my Jeffrey Lipton mug was taking up the space in my backpack that could have otherwise been devoted to doughnuts. I enjoyed a couple bites of both the dark chocolate sea salt and the maple-glazed flavors and passed the rest off to my very pleased Uber driver.

Dear Portland: I’m sorry I ever made you feel like you weren’t good enough to fit inside my idealized image of Maine. I’ve since learned that Maine comes in many flavors, and yours is definitely worth tasting.

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