Due North – A Long Weekend in Portland, Maine

The heat came early this spring. By May, it was already hot. I was happy to head north in early June for a long weekend in the cold. June, in Maine, is still cold. I learned this the hard way on my first visit to Maine.


I first visited Maine when I was in college. My college boyfriend had family there, and one summer we cobbled together a very cheap ticket on Southwest Airlines–one that involved something like four transfers–and flew east for a visit. We flew into Portland, where my boyfriend’s cousins picked us up. After one night in town, they bundled us into a car and we drove north, towards Bar Harbor. It was June, and I arrived expecting summer weather. I packed swimsuits and sundresses, dreaming of long days by the water. In reality, it was cold and damp, and I couldn’t spend more than five minutes by the water — really, any body of water, be it the Atlantic or the little river that ran behind the house–without being eaten alive by mosquitos. So much for my romantic idea of a beach vacation. One day, we drove to an L.L. Bean outlet store and put together a more appropriate wardrobe for me, cherrypicking things out of the children’s section (an 80s inspired anorak, some heavy cotton sweaters). I gave up on the idea of spending my days sunning by the beach–for there was no sun, and the beach was rocky and cold. Most days, we sprayed ourselves down with bug spray, and went hiking in the woods instead.


On this trip, we had roughly three and a half days in Portland. We traveled with friends, and had no specific goals, aside from eating well. We basically ate our way across Portland, with some detours for brewery visits, and for art. It was a quick and shallow visit, but one that I hope laid the foundation for longer future trips.

One of the lighthouses at Two Lights, a location favored by artists like Winslow Homer and Edward Hopper.

Beautiful, with a haunting, somewhat melancholy sense of isolation — heightened by the feeling of standing at the edge of the world — the Maine coast has attracted artists since at least the nineteenth century, but probably since the dawn of (human) time. In more recent times, Winslow Homer and Edward Hopper both found their way to Portland. There are the famous artists’ colonies at Oguinquit and on Mount Desert.

Our visit coincided (unintentionally) with Portland’s First Friday Art Walk. The event had a warm, communal feeling–tables featuring work by students from the Maine College of Art and Design lined both sides of Congress Street, and the walk down Congress felt less like a commercial event than a promenade or evening paesaggio. Friends stopped to greet friends, students table-hopped to check out each other’s work. Community groups set out tables to recruit volunteers. There was live music — including a steel-pan drum group where the youngest drummers looked to be about ten or eleven years old. There were dogs. The atmosphere reminded me of the friendly Midwestern college town where I spent a chunk of my childhood, a mixture of warmth and joie de vivre and tender community pride.

A few days later, we drove south to visit Ogunquit. It is a small town, about 45 minutes (by car) south of Portland. Situated in the midst of a string of shore towns, each hawking a distinctive category of experiences (Kennebunk/Kennebunkport offered “historic town center/architecture” and “beaches,” another town had motor courts, cabins, and a water park), Ogunquit’s marquee experienced was “art”–you could buy art, you could look at art (there is a nice little museum in Ogunquit, but we didn’t have time to visit it), and you could make art (e.g. workshops in plein airt painting, workshops in bookbinding, watercolors, and other media). We popped in and out of a couple of small galleries, but spent most of our time at the Barn Gallery, home of the Ogunquit Art Association. On our next visit, I’d like to take this walking tour of Ogunquit, though I suspect that on our trek from the far end of town, where we parked our car, to the Barn, we walked past many of the points of interest in ignorance. The day of our visit, the weather was raw and overcast. Even under those conditions, with the sea a steel grey and that soft, pearled light, I could see why generations of artists — especially plein air painters — came to this little seaside town.

silver light over a mostly empty strand, Kennebunkport
beach roses on the way to the beach, Kennebunkport

I had low expectations for Ogunquit. In California, I’d grown used to seeing beautiful places, once havens for artists, transform into something else–most often some cross between an open-air mall and billionaires’ club. Pity California: our beaches are public, but our beauty is for sale. I was pleasantly surprised to find living communities, and not just communities of midcareer or established artists, but also students, people just beginning to explore the idea of making a life that involves making art. Without this sense of the future, it’s all too easy for these towns, so rich in history, to rely on the concept of heritage, and ossify into set pieces. Just look at Venice, burdened with historical wealth, struggling to continue as a living city, searching for ways to push against the unwelcome fate of becoming an open-air museum.

But we came to Portland to eat. Or, as I giddily told our server on our first night in town, “We’re here to commit the sin of gluttony!”

These days, thanks to a constant stream of media coverage, Portland is widely known as a food destination. Visitors–like us–travel long distances to taste the region’s bounty. Tourism has long been a pillar of Maine’s economy. The state even calls itself “Vacationland.” But tourism can be an ugly industry: exploitative, extractive, mostly offering locals low-wage, transient service jobs. How does one create good, stable jobs and keep wealth in the local community? This is a perennial question for tourist economies. In recent years, more and more vacation destinations are turning to the creation of a “farm-to-table” or localvore ecosystem, as one potential answer to this tricky question. Is it all hype? Does it work? It would be interesting to see some numbers.

Covid threw a wrench into all this. In the U.S., at least, remote work gave workers the opportunity to exchange their pricey urban (or suburban) dwellings for less-pricey (or equally pricey but nicer) homes in beautiful places like Jackson Hole, Wyoming. Our friend, who works for a Portland nonprofit that provides social services, confirmed that this influx of monied new residents, coupled with the ongoing shortage of housing, has driven up the cost of living in the city. (Portland has the same issue as every other American town, it has an inadequate supply of existing housing, and this constricted supply is not being replenished by new development.) With that, I wonder, are people paddling harder just to stay in the same place? Even if visitation rates are soaring, and tourists are (or were, prior to rising inflation rates) spending more, is it enough to get beyond survival mode and into wealth creation (or maybe just… stability)?

We still ate our way across Portland. We had a long, leisurely, and very fun dinner at Chaval, where the staff was warm, hospitable, and indulgent. Our server didn’t even blink when my husband ordered a hamburger for dessert. (Probably because I ate more than half of his “dinner” burger.) The burgers are very good, so if you read this and decide that you, too, want to have a burger for dessert, know that none of us will judge you for this choice. Chaval’s tapas-style small plates showcase local ingredients. A surprise hit: the beet-pickled deviled eggs, which came topped with a slice of jamon.

deviled eggs, Chaval

Portland has no shortage of good bakeries. Our three favorites were Two Fat Cats, Scratch Baking (a good place to stop and pick up a snack on the way to Two Lights), and Norimoto Bakery. Norimoto won a James Beard Award shortly after our trip.

I saved the best meal for last. On our last trip to Portland, I ate khao soi from the Honeypaw in my hotel room while the guys went out to a wine bar. It was one of my favorite meals on a trip with several good meals (cocktails at Portland Hunt & Alpine Club, fries at DuckFat, a long dinner with lots of wine at Fore Street, oysters and seafood at Eventide). We ate at the Honeypaw on our final night in Portland, and it was everything I hoped for, and more. It’s really something special when everything comes together, especially on vacation, when the anticipation builds in another layer of expectation.

the crudo course at the Honeypaw

After three trips to Portland, I am just starting to get to know the place. As fun as it’s been to play tourist, and eat my way through Portland, I think this will be our last “food”-centered trip. I’d like to have more than a passing acquaintance with this place, and know the area in a deeper way–the history, the land, the ecology, and the artists, past and present, for whom this difficult and beautiful land played both cradle and crucible.

Travels with Bear

I almost always travel with my Pomeranian, Bear, so before we go anywhere, I spend a lot of time researching dog-friendly hotels, restaurants, and attractions.

a canine friend hanging out in a window

We found Portland friendly and accommodating to dogs. We stayed at the Hyatt-Old Port, and the front desk staff generously offered Bear multiple treats over the course of our stay. Most restaurants allow dogs in their outdoor seating areas. Portland is a very walkable city, with lots of parks.

view from the Eastern Promenade

Bear and I like the Eastern Promenade trail. If you start in the Old Port area, the trail will take you through a variety of different neighborhoods. The Eastern Promenade itself offers sweeping views of the water, and there are often food trucks offering delicious treats. I got a delicious hand roll from the Mr Tuna truck, and if we didn’t have dinner reservations that night at Chaval, I would have filled up on hand rolls and ice cream (from the neighboring ice cream truck).

Getting there: This time, we drove. Sometime in the future, I’d like to take the Amtrak Down East line from Boston. You can also hop between various shore towns (Wells, Kennebunk, Ogunquit) on the train, though you might have to take a shuttle bus to get into town.

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