A Weekend in Portland

Day 1: The Scavenger Hunt

“Whoa, that’s a wicked nice camera.”

Using a hand to shield his eyes from a sun that hadn’t yet risen, he aimed the statement at me and the Nikon tethered to my neck, oblivious to the fact that his dog’s leash had just become tangled around a tree. I was kneeling on the ground—absentmindedly snapping pictures of a purple sky on the verge of blossoming into a collage of pink and orange—trying to discern whether the boats bobbing on the horizon were actually used for fishing, or if they were just permanent fixtures of the scenery.

                                        Waiting for the sun to rise over Portland.

I offered the man a smile in response to his observation, thinking that would appease his curiosity, but I was wrong; just like I’d been wrong to think I’d be the only person in Portland waiting to see the sunrise over the Eastern Promenade. Retrospectively, that had been naïve to the point of foolishness as it’s difficult to resist the beauty of coastal Maine, especially illuminated in fall sunshine.

“Are you a journalist or somethin’?” the man probed innocently. His equally curious chocolate lab, whose leash was still woven tightly around the tree, stuck its nose deep into my discarded backpack as if sniffing out clues for his owner.

“Sort of. I’m a travel writer. It’s my first time in Portland,” I admitted.


Early-rising Portlanders walking their dogs along the Eastern Promenade.

These words seemed to echo over the hills and into the ether, magically attracting other early risers, and soon I was surrounded by a small group of Portlanders eager to learn how I’d come to be in their city, and even more eager to offer recommendations.

“You from away? Well, if you want a real view then you gotta go to the top of the observatory,” said a middle-aged man with pepper-colored hair cradling an energetic terrier.

“Oh, you’d love Harvest on the Harbor,” offered a woman decked out in running gear, although her accent made it sound more like Hahvest on the Habah. “It’s a food festival this weekend goin’ on by the watahfront.”

“Have you tried any Portland brews yet? I think you’d like Gritty’s, but Shipyard also does tastin’ tours if you’re into that,” announced the owner of the chocolate lab.

I scribbled their suggestions on a piece of paper, itching to inject some local flavor into my itinerary. I’d arrived in Portland less than twenty-four hours ago from New York City, with no explanation for coming except that I’d never been, and no concrete plans aside from eating as much lobster as I could stomach.

Thirty minutes later, after thanking everyone for their thoughtful suggestions and capturing a few more stellar photos of the sunrise, I wandered into The Front Room; a local breakfast spot recommended by the owner of the terrier. I grabbed the only free seat at the bar, and a moment later, someone else decided to take a stab at guessing why I was in Portland.

Potato gnocchi at the Front Room
          Potato gnocchi at The Front Room

“Did someone send you on a scavenger hunt?”

At first, I wasn’t sure what she meant. It was nine in the morning after all, and the waiter hadn’t yet brought my coffee and potato gnocchi, the coffee being most important. In response to my confusion, she pointed to the list on the paper in front of me, now scribbled with incomprehensible notes like, “PO closes at five,” with PO being the Portland Observatory, and “M recommends Gritty’s,” with M being Matt, the owner of the chocolate lab.

“Oh! No, no. This is my itinerary,” I laughed, now understanding her train of thought. “It’s my first time in Portland.”

“How exciting! Did you come here alone?”

I was slowly realizing that there’s no such thing as strangers in Portland, just future friends and neighbors that have yet to be introduced. By virtue of visiting the city, newcomers unwittingly agree to share their name and a few good stories with anyone curious enough to ask, which is largely everyone.

After sharing my name, two more cups of coffee, and a longwinded story about a rogue road trip I’d taken along the coast of northern France back in 2011, the woman– Julie–suggested I make a pit stop at the local flea market, cleverly called the Portland Flea-For-All. I subsequently added the spot-on suggestion to the top of my to-do list, thanked Julie for keeping me company over breakfast, and eagerly headed into town.

                                   The cobblestone streets of Old Port

Parsing together the slew of tips I’d received over the course of the morning, I spent the remainder of the afternoon digging through racks of vintage clothes at the Flea-For-All, wandering the cobblestone streets of Old Port, dining at Duckfat for lunch and Otto Pizza for dinner, and finally ending my adventure with a tall glass of the Black Fly Stout at Gritty McDuff’s. While massaging my sore feet at the end of day, I realized I’d answered Julie’s question incorrectly; it seemed I had been sent on a scavenger hunt after all.

Day 2: The Mystery Woman

“And you must be Samantha.”

I instinctively glanced down at my clothes, searching for monograms, misplaced name tags, or anything that would’ve revealed my identity, but I found nothing. Chuck, whose name was laminated and hanging proudly around his neck, seemed to have an uncanny ability to discern the members of his tour group based entirely on interactions over e-mail. He happily informed me that his son had also graduated from my alma mater and was living in New York City, and I racked my brain for when I had shared either of these facts with him.

Chuck was one of the guides for Maine Foodie Tours, but he acted more like a long lost uncle at a family reunion; talking to you as if he’d watched you grow up, and asking questions about your life as if he merely needed a reminder. The tour had been recommended to me by a representative at the Maine Office of Tourism, who responded—at lightning speed—to my last-minute e-mail asking about the best places to eat in Portland. The tour covered the culinary hot spots of Old Port, and included local favorites like the Harbor Fish Market, Two Fat Cats Bakery, the Stonewall Kitchen, and even a beer tasting at the Shipyard Brewing Company, which my unofficial tour guide, Matt, had recommended the day before.

Chuck showing off his lobster skills at the
    Chuck, showing off his lobster skills at the Harbor Fish Market

Over the course of three hours, Chuck led me and nine other out-of-towners on a whirlwind tour of the city, where we tried samples of Maine lobster, local cheeses, chocolate truffles, homemade jams, and even whoopie pies. We washed it all down with honey mead and (what felt like) unlimited samples of Shipyard beer, and by the end of the tour, I wasn’t sure whether I needed to go to the gym or take a very long nap.

Before abandoning the other group members, who now felt like family, too, I pulled Chuck aside and gave him a rundown of the things I’d already done and seen in Portland, and asked if there was anything important I was missing.

“Well, you’re a writer,” said Chuck, knowingly, “so you can’t leave without seeing the Longfellow house.”

He was referring to Henry Wadsworth Longfellow, the famous poet, whose childhood home still stands in Portland as a public museum maintained by the Maine Historical Society. Seeing the place where Longfellow had written some of his most famous works, including several odes to his hometown, seemed like the perfect way to end my visit. Writing down Chuck’s detailed directions (“Call me if you get lost!”), I set out to Longfellow’s house, which seemed like a surprisingly natural thing to do and say.

As luck would have it, I arrived just in time for the last tour of the day, with only one other couple joining me. Before starting the tour, our guide, John, reminded us that no photography was allowed once we entered the house. Slightly crestfallen, I placed my wicked nice camera back in my bag; however, I wouldn’t have had time to take pictures anyway, as John was spitting out facts a mile a minute, speaking of Longfellow and the house as if he’d grown up there himself.

“The last living relative of Longfellow’s to live in this house was his sister, Anne Longfellow-Pierce, who was widowed at an early age, and stayed in this home until her death in 1901. Prior to her death, she arranged a deal with the Maine Historical Society to turn the home into a museum and memorial to her famous brother, on the grounds that everything be left exactly as she instructed,” he recited.

“In order to ensure her request was honored,” he continued, “she compiled hundreds of letters, notes, and photographs to tell the story of every artifact, item, and person that ever resided in this home. Everything down to the wallpaper and carpets was meticulously noted by Anne. Everything, that is, except the portrait of the mystery woman.”

John paused for dramatic effect, and then pointed to a framed pencil-sketch of a woman on the wall of the guest bedroom, where Longfellow had stayed with his second wife, Frances Appleton, on their honeymoon.

“Now, usually I would end the tour on this note,” said the guide, ominously. “But, as it so happens, previously lost documents of Anne’s have resurfaced in the last two weeks, revealing the identity of the mystery woman. She is Elizabeth Longfellow, another sister of Anne and Henry’s, who died of typhus in this house at the age of twenty.”

A stunned silence fell over the small group as we digested this information with a mixture of awe and curiosity. I groped at my camera, wishing desperately I could capture a shot of Elizabeth looking forlorn in her portrait, staring off into the distance at nothing and no one in particular. Finally, John broke the silence.

“Personally, I liked it better when we didn’t know her identity. It added a certain mystique to the house,” he said, as his eyes lingered on the sketch for a second longer. “Now, does anyone have any questions?”

The hands of my fellow tour mates shot into the air, and they began quizzing John on why Anne had never remarried, where Longfellow sat when he penned The Rainy Day, and other fact-based questions whose answers were surely housed somewhere within the hundreds of notes and letters catalogued by the poet’s sister.

My question, however, couldn’t be answered by John, and it was most likely missing from Anne’s meticulous records. My burning question was how Elizabeth had managed to keep her identity a secret for so long in the convivial city of Portland, where there’s no such thing as strangers.


For more photos from my weekend in Portland, click here.

8 replies »

  1. My eldest son works in Portland and lives with his family in Freeport. This means that we visit Maine pretty well every year. Although I recognise some of the sights you describe, I’ll keep this well written tale in mind for next time we come over. We were last there in September and had a quick visit to Portland for ice creams for our three granddaughters, after spending time at the light houses south of the city. Thanks also, for following my humble blog.

    • That’s wonderful. I’m jealous you get to go often. It was my first time in Portland, and one weekend certainly wasn’t enough to see and do everything. The culinary scene alone is comparable to my borough in New York City, and I could’ve eaten every meal at a different restaurant without covering all the good ones. I’m glad I could recommend some new places for you. Thank you for the kind comment!

  2. Such a great city! I grew up in New Hampshire, so a couple of times a year my mom and I would take a drive up to Portland. One summer, we rented a house on Little Diamond Island in Casco Bay – the harbor photo you’ve got there is actually where the ferry takes off from. Portland is a beautiful little city – so much character and wonderful dining options! Definitely something I miss now that I’m in Chicago!

    • That’s wonderful, I agree; Portland is an amazing little city with a million secrets. I’d heard great things about Little Diamond Island, but quite frankly the weather in October was too cold for me to enjoy the beach or water. I’ll definitely have to return in the summer, though!

  3. Reblogged this on The Epicurious Texan and commented:
    Below is a GREAT weekend trip idea! I’ve been to Maine once before and though it was only briefly, I definitely fell in love. Lucy is spot-on about there being no such thing as a stranger, something that pulls at my Texan heartstrings! Thanks Lucy, for sharing! 🙂

  4. I was down in Portland a couple of years ago and so loved it! Especially Newport, so many things to see. After reading your post though, I may have to make a second trip! thank you for following me 🙂

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