26 Foggy Hours in Portland

As I sat in the South Station Bus Terminal that early May morning eating my yogurt/granola/berry parfait (thank you, Melting Sun), one could be forgiven for mistaking me for a miserable, sleep-deprived traveler; while the latter was certainly true having to had waken up at 5 AM to catch the 6 AM commuter rail out of Providence, I truly could not have been more excited for my 8 AM bus to Portland—even if my body language wasn’t showing it. I’ve called New England home for a few years, but had not yet made it to Maine. This trip was my first visit to the state, and I was determined to uncover whether its nickname of “Vacationland” was warranted. Seeking to enjoy the transitions of spring, I booked my trip for a midweek excursion to the state’s biggest city, Portland.

When I booked my trip, I checked the weather app to ensure I’d get that wonderful, cool yet sunny New England spring. Nature had other plans: by the week of my trip, most of the region was blanketed in rain and clouds, and Portland was no exception. I had already taken the days off of work, and part of me was wishing I just stayed in Providence and saved on travel fares—after all, if I wanted to enjoy a small, quirky New England city in the rain, I could have just stayed home. Yet I remained to determined to pay my first visit to Maine’s largest city.

In many respects, Maine is very similar to its New England brethren, and captures the essence of the region to an almost quintessential degree (one should hope, given that the state comprises almost half of New England’s area). Maine has a smattering of elite colleges (Bates, Bowdoin, Colby), a strong state university (UMaine in Orono); seafood and its harvesting consist a significant part of the state’s culture, diet and economy (perhaps the most of any New England state); and a populous, waterfront city serves as the state’s first introduction to many.

But Maine is unique in many regards, not the least of which being its politics. New England, generally, is a deep blue bastion, save for its two northernmost children. New Hampshire fashions itself a libertarian state: Live Free or Die, as the state motto goes. But recent Republican efforts in the state aimed at eroding trans rights, its recently-elected MAGA-friendly (formerly anti-Trump, and perhaps now MAGA-regretful?) governor, and its continued rightward drift show that in the Trump era, the state is simply conservative, moderately so at best—the Alberta of New England. That the state’s entire congressional delegation is Democrats seems like a fluke. Vacationland, however, is much more of an enigma. Senators and governors often win in pluralities. The state has an all-Democratic House delegation (despite the 2nd district voting for Trump in 2016 and 2024), and GOP and Independent Senators, the former of whom has a historically flippy-floppy relationship with the GOP. Current governor (and now Senate hopeful) Janet Mills had a high-profile spat with the president in March, culminating in a legal battle over trans athletes in which the feds ended up backing down. Her main primary opponent, Graham Platner, is a Marine-turned-oyster farmer running on a progressive platform and his purported ability to speak to Trump voters and bring them in to his fold, who remains the frontrunner despite scandals including controversial Reddit comments and an an SS tattoo that threatened to upend his campaign. In 2023, the state had a much-watched (albeit ultimately unsuccessful) ballot measure to create the first modern public utility in the nation. So yes, Maine is unique.

This political landscape makes Portland even more interesting. While cities often outflank their respective states to the left, Portland often also outflanks its peers in New England. The city passed (2020) and enacted (2021) a rent control measure (which has been continually protected by voters) now being used as an example for similar efforts in Providence; it voted to divest from Israel in 2024; and while New England is known for its queer hotspots (Northampton, Mass. may come to mind), Portland is, at least anecdotally, queer to the point where a “gay bar” is redundant, at least for a city of its size. Only one—Blackstone’s in the West End—remains.

Portland’s peninsula, where I focused my journey, is fairly small. Walking is not an inconvenient or especially time-consuming way to get around, so the location of my lodging (at least when booking) didn’t matter too much to me. I was lucky that my hotel was right next to a GP Metro bus stop, then, when the weather proved to be much colder and wetter than initially anticipated. Since I arrived fairly early in the morning, I couldn’t check into my hotel for a while, but they were kind enough to hold my bag. After that, I walked five minutes up Park Avenue past Hanley Field and just about up to Deering Oaks Park.

My destination, nationally-renowned local donut shop The Holy Donut, was where I could cross off my first Portland to-do: try a potato donut. While not unique to Maine, Portland has definitely captured critical attention for them. However, Portland captured my attention for different reasons that morning. Despite most of the city being blanketed in fog, I couldn’t help but notice the surprising density in a part of town fairly close to the highway and near the edge of the peninsula. And not only was there density, but there was a diversity to it, from classic New England triple-deckers to mid-rise brick apartment complexes characteristic of the postwar years to even newer and taller apartments (albeit in the distance and partially shrouded by fog). To me, Portland—at least the peninsula—feels like it out-cities its peers of similar size, and that’s not even mentioning its growing bike network that puts much of my home city of Providence to shame.

After finishing an absolutely delectable toasted coconut potato donut, I hopped GP Metro’s 5 bus for a short (<4 min) trip into Downtown Portland. Taking in the classic old American downtown architecture with a bit of New England flavour, I made my way to Monument Square, stopping in galleries, a map store, and a café. At Monument Square, I checked out progressive bookstore Longfellow Books before continuing to the Old Port, full of boutique local shops and, of course, boats! Following a brief rideshare to Cape Elizabeth to visit the Portland Head Light and the adjoining Fort Williams Park, I returned to the Old Port before finding a place for dinner.

I settled on Highroller Lobster Company for, of course, a lobster roll—plus a drink at the bar. While the name might evoke images of a posh, snobby, upscale dining experience, I found Highroller to be anything but. The building was quaint and warm, both in atmosphere and temperature (much appreciated after getting soaked during my search!) The restaurant has certainly kept its original food cart humility while simultaneously becoming one of Portland’s more celebrated and popular eats (alongside ever TikTok popular Eventide Oyster Co.) Dessert for the night—a cool, albeit weather inappropriate, scoop of gelato—was acquired at Gorgeous Gelato. With many ingredients imported directly from Italy, they have the stated aim of providing “the best gelato west of Italy.” If their ricotta fig flavour is anything to go by, they’re certainly in the running.

I didn’t have much time the next morning, as I had changed my train to an earlier one to make it back to Providence before seeing Japanese Breakfast at MGM Fenway, so after enjoying one last Holy Donut, I crossed the street to wander through Deering Oaks Park, the largest park in the city. Even when covered in fog, the park is wonderful—if anything, the fog elevated its ambience. Taking in the trees’ springtime return of color, I made my winding way through the park to the Portland Farmer’s Market, one of the items on my travel list I would have been remiss not to visit. While I’m sure that the weather tempered turnout, it had a wonderful selection of local artisans, growers, bakers, and more. If you’re visiting Portland from late April to late November, the market in the park is open on Wednesdays and Saturdays from 7am to 1pm—going by their 2025 calendar, 26 November will be the last outdoor market, so there’s still time from now if you don’t want to wait until April.

As a strong supporter of rail travel, it pains me to say that I much preferred my less comfortable but quicker bus up to Portland over Amtrak’s Downeaster service on my return—it was nice seeing the scenery of the Downeast and stopping in less-visited cities in Maine and New Hampshire, but as we approached (more appropriately, crawled towards) Haverhill, I yearned for the end of the ride so that I could make my North Station-Orange Line-Back Bay connection to the MBTA Commuter Rail back to Providence. That being said, there was a silver lining on Amtrak: the café car serves toasted coconut donuts from The Holy Donut.

Of course, this is not to paint a picture of Portland as the perfect, idyllic New England port town—although it certainly has the potential to be. Metro’s services aren’t as frequent or far-reaching as they perhaps should be (I ended up walking back to my hotel in the dark after dinner); the Amtrak station is a little removed from the rest of town (perhaps there’s a solution in the works); but if one spends any time in Downtown Portland, one problem is immediately, glaringly obvious: the homelessness and drug epidemics. As of 2024, 2,695 Mainers were homeless, many of whom live in Portland. Portland has also served as a face for the return of meth, which now competes with fentanyl as the drug of choice—yet one without a naloxone equivalent to reverse its effects. While it shouldn’t have to be noted, it’s worth bearing in mind that there are many housed drug users, and just as many substance-free homeless individuals; but it is not difficult, and all too common, for one of these afflictions to quickly spiral into the other.

Portland’s efforts (and lack of great success) in tackling these crises have manifested in a stark manque of public restrooms downtown, of which there are only six. Having to frequently need use the restroom in Portland—which I did—is a Kafkaesque nightmare. Some members of the public explain, even defend Portland’s dearth of public restrooms as a necessary price in countering “the homeless problem.” Simultaneously, Redditors and columnists alike lament the “dirtiness” on the street and deride the homeless. From the comfort of their homes, they insist there are plenty of social services to go around, implying that the problems the homeless population faces are their fault alone. They dislike them yet want no defined place for them to go, at least not within their line of sight.

But my plight in finding a public restroom is nothing compared to the daily life the homeless in Portland must endure. I could have returned to my hotel and used the restroom there, as I was fortunate enough to be able to afford a hotel; I could have paid for a coffee at one of the few shops with a restroom, asked for the code, and used it there; meanwhile, Portland’s homeless population downtown is greeted by “Customers Only” signs. They must face, often without protection, the harsh weather coastal New England can see, from freezing winters to torrential downpours like I saw on my trip. Access to a restroom should not be limited to the public library or city hall, and should not have an access fee of a $5 (at least!) drink.

The solution to homelessness in Portland is not restricting access to restrooms, just as it is not moving the RIPTA hub out of Kennedy Plaza in Providence: it is, first and foremost, housing. The solution to the drug epidemic is not removing sharps boxes and shunning its victims: it is treating it as the urgent medical and public health crisis it is, providing treatment and reducing harm, as is being done in Providence.

All of that being said, I truly did have a wonderful time in Portland: the city is one of New England’s jewels and is absolutely worth a visit. Bus and rail connections make getting there a breeze. Maine, like all New England states, has a local flair that makes its cities that much more interesting. My advice: give Vacationland a try. You’ll find out why it’s called that soon enough, even if “vacation” just means a day trip.

And now, my (admittedly touristy) Portland recommendations:

If you enjoyed this article, please consider donating to Preble Street or other Maine-based homelessness support networks.