Kennedy School in NE Portland © McMenamins
McMenamins Kennedy School is a century-old Portland elementary school turned hotel, with a brewery in the old girls’ loo, a jazz-themed secret room and detention served with a side of whisky. I mean, obviously I had to check it out.
I got sent to my room… then took a dip and moved bars twice, and nobody, not once, told me to sit up straight. Which is lucky, because several bevvies in, I’m not sure I could have. Welcome to McMenamins Kennedy School, the Portland hotel where being kept after class is the whole point.
Officially, I was there for an art tour. Unofficially, the bars, the pool and the bevvies staged a fairly successful coup.
The building, on NE 33rd Avenue in Portland’s Concordia neighbourhood, still looks much as it did when it opened more than a century ago… a proper Italian Renaissance Revival-style school with warm walls and long wings stretching out either side of a colonnaded entrance. Except instead of kids racing for the bell, it’s guests wandering the halls in dressing gowns, with no hurry to be anywhere.
The history of McMenamins Kennedy School, Portland’s converted school hotel
Kennedy School © Aleney de Winter
The Kennedy School’s story starts in 1913, two years before the present building opened, when the first classes were held in portable one-room buildings on the site. There were just 29 children. The location was considered pretty remote, sitting three blocks beyond the end of the nearest streetcar line. It was apparently rural enough that an ordinance prohibited people from shooting rabbits from the streetcar. No, seriously… this is Portland.
The school opened its doors in 1915, named for local landowner John Daniel Kennedy, who donated artwork for the school’s 1916 dedication, and for the next sixty-odd years it did exactly what schools do. Though it moonlighted as pretty much everything else in town too. When classes weren’t running, Kennedy doubled as the neighbourhood’s town hall, a polling place on election day, a Red Cross blood drive venue and a spot for paper and tin can collection drives. It also served as a weekend playground and a flood-relief shelter. This was never just a building where kids learned long division. It was where a whole neighbourhood happened.
Which is why, when the beloved school finally shut its doors in 1975 due to dwindling enrolment, the neighbourhood took it just about as well as you’d expect. Technically, the school continued to be used as a temporary facility for other Portland schools until 1980, when it finally closed completely.
The city took one look at the ageing building and reached for the wrecking ball, but former students, past PTA presidents and a stubborn coalition of neighbours spent years fighting off demolition order after demolition order… because nobody in Concordia was prepared to let their old school become a car park without a fight. Several ideas were floated for the empty building, including a retirement home and, bafflingly, an indoor soccer facility, before Portland natives Mike and Brian McMenamin, who’d already made a habit of adopting condemned buildings the way some people adopt strays, bought the school in spring 1997.
A few months later, the original principal’s bell was rung on the front steps to mark the reopening as the very Portland and utterly unique Kennedy School Hotel, just the kind of theatrical flourish this building deserves.
Art that turns every hallway into a gallery
Words of Wisdom by J. Joy at Kennedy School © Aleney de WInter
Once you’re inside, you understand the fuss. McMenamins employs a company historian, Tim Hills, whose job on this project was tracking down blueprints, old class photos and firsthand memories from former students and teachers, then handing all of it over to a small army of artists, nearly fifty of them over the years, to turn into paintings, mosaics and wood panels covering every wall, ceiling and doorway in the building. The house style has earned its own nickname, historical surrealism, because every piece is anchored to something that genuinely happened here and then given just enough creative licence to make you stop mid-stride and squint at a wall.
The first stop on our art tour, right by the main entrance, sets the tone. Four bas-relief panels flank the doorway, and they turn out to be full-size reproductions of Luca della Robbia’s 15th-century masterworks, originally made for a cathedral in Florence. They were cast in Boston and gifted to the school for its 1916 dedication by John Daniel Kennedy, the school’s namesake, then spent time on display at the Portland Art Museum before McMenamins restored and reinstalled them in their original spot in 1997. Children dance, play trumpets and drums and read, exactly as they would have for a Renaissance cathedral, except now they’re watching guests wheel suitcases past them instead of monks.
Then for no apparent reason other than that McMenamins love a little whimsy, there’s a bronze gong display, which I am quite taken with.
Lobby artwork © Aleney de Winter
There are plenty of original details lurking behind the art. The former classrooms still have chalkboards and cloak rooms, original 1915 bas-relief panels survive… even the kid-sized drinking fountains are still there. It means you keep getting little jolts of the building’s actual past among the murals and mosaics, rather than feeling as though you’re walking through a hotel decorated to look like an old school.
The painting Words of Wisdom, by J. Joy, is an good example of the way Kennedy School’s artists fold the building’s history into the artwork. Another smaller painting called “My Modigliani” was painted by Carol Manfredi, a 1949 Kennedy School graduate, as a tribute to her old art teacher, Mrs Stella Pietila. Manfredi went on to study art formally and realised, years later, that her tall, long-necked teacher had always resembled the elongated figures painted by Italian artist Amedeo Modigliani, so she tucked a small replica of one of his works over Mrs Pietila’s shoulder.
A little further on again is a genuinely serious piece among all the whimsy, a triptych by the late Portland artist Charlotte Lewis that’s part tribute to the Yoruba religion and part portrait of jazz legend John Coltrane, painted in gold script with lines from a traditional West African prayer. It’s one of several Coltrane and jazz-themed works scattered through the building, a thread that Kennedy School has clearly kept pulling on.
One of my favourites is something altogether more playful, a Punch & Judy-style puppet theatre facade. It’s a wonderfully unexpected little piece to find tucked among the murals, mosaics and photographs of a former Portland school.
Where to drink at McMenamins Kennedy School
The Boiler Room at Kennedy School © McMenamins
The building’s sense of humour never lets up. Reception is in the old principal’s office, which makes checking in the first time in your life that a summons to the principal’s office has ever been good news.
Then there are the bars. Lots of them. McMenamins has managed to tuck drinking spots into former classrooms, the old boiler room and, naturally, the girls’ bathroom, so wandering the school with a drink in hand feels less like going to a hotel bar and more like discovering the school has developed a very serious drinking problem.
The onsite Concordia Brewery operates out of what used to be a girls’ bathroom, thoroughly renovated, of course, though there’s something delightfully Portland about ordering a flight of beers from a converted loo and being asked if you’d like tasting notes. The pink tiling on the walls has been left exactly as it was, a small, deliberate wink at the room’s former life, and the artwork on the brew kettles carries the joke further still, with two stern principals, two long-suffering early students and, high in the south-west corner, a painted recreation of an old rite of passage. Kennedy boys used to fling open the door and sprint the length of the unusually long room, hoping to make it out the far side before a teacher caught them.
Down in the basement sits the Boiler Room bar… all exposed pipework and industrial charm, doing the heaviest lifting of anywhere in the building for pure atmosphere. The pipes and radiator railings snaking around the stairs were welded together in 2008 by Jeff Allen, a McMenamins plumber with an artist’s eye, using salvaged fixtures from the company’s other historic properties. But before any of that, it was the domain of a real school janitor named Steve Hutton, a bagpipe-playing Scotsman remembered by students for teaching students the Highland Fling and, more improbably, for showing a kid with a freshly shattered left wrist how to throw right-handed instead. That kid, Don Johnson, went on to pitch for the New York Yankees.
There’s Detention, which used to be the janitor’s room. The old wood-burning stove is still parked in the corner, decades cold, like a retired staff member nobody had the heart to move on. I spent a very happy stretch of my afternoon there, day drinking in a room that once smelled of mop buckets, feeling like I’d finally cracked the code on what detention should have been in a perfect world.
The Honors Bar © McMenamins
If Detention is where the naughty kids go, Honors Bar is for the ones who actually did their homework. Tucked into another cosy little room, it’s deliberately scholarly, with classical and operatic music playing while the grown-ups work their way through cocktails, beer, wine and spirits. It’s also adults-only, so despite the gold-star theme, this is one classroom where the kids aren’t getting in.
Cypress Room has a completely different personality. The former classroom is now a rum-loving little hideaway, with an extensive international rum selection, a full menu and island and reggae music that may even be spinning on vinyl. There’s a Bob Marley quote painted above the bar, plus a patio out back for warmer days.
There’s also the Courtyard Restaurant, occupying the old cafeteria and spilling outside into the courtyard. It’s more restaurant than drinking den, with a full-service bar, so it’s a good option when you want an actual meal with your drink rather than another round of wandering-school-with-a-pint.
And if you’re heading to the movie theatre, you don’t even have to abandon the booze. The Kennedy School Theater Bar occupies the former classroom that serves as the cinema’s lounge and lobby, where you can grab a drink, pizza or popcorn and have it delivered to your table during the film.
By this point, you may have noticed a problem. There are enough places to drink at Kennedy School that you can genuinely spend an afternoon moving from one to the next without ever having to leave the building. Which, tbh, is probably the best reason to stay a night or two.
Ghost stories (allegedly)
Whimsical features © Aleney de Winter.
Stick around long enough and someone is bound to mention the ghosts. Because of course they will. The McMenamins Kennedy School Hotel has a reputation as one of the more haunted McMenamins properties going, and the stories cluster in oddly specific spots. A tap on the foot in the middle of the night in one particular guestroom, the sound of children laughing near where the old maypole dances were held and a women’s bathroom off the main hallway that’s earned a name as the property’s unofficial ghost sighting hotspot. There’s even a painting of a girl, based on an old class photo, that folk will tell you is haunted. More than one guest swears they’ve seen her sitting in a chair nearby in the same ‘fit, right down to the bows on her shoes.
None of this is documented in the building’s official history; it’s more anecdote and folklore. But it is a very old school, it was after dark, and I am, at my deepest core, a bona fide coward, and I’d had enough McMenamins ales for my imagination to be firing. So in the hallway between bars, I may or may not have moved fast enough to achieve a personal best.
The Testimony Secret Room at the Kennedy School
The Testimony Secret Room @ Aleney de WInter
Somewhere in the building, if you’re patient and a bit lucky with your timing, there’s also a secret room. The Testimony Secret Room only opened in December 2025, an entire hidden installation dedicated to jazz legend Charlie Parker, painted floor to ceiling in glow-in-the-dark paint. It’s more than just an abstract homage to Jazz, Charlie Parker actually played Portland as part of a now-vanished jazz scene that once thrived along Williams Avenue, a few kilometres from where Kennedy School stands today.
The installation itself is based on Yusef Komunyakaa’s 1997 work Testimony, which explores Parker’s life, with fluorescent and phosphorescent paintings, colourful cityscapes based on places Parker lived and performed, portraits of musicians he influenced and 14 scrolls carrying words from Komunyakaa’s work. The three artists behind it, Eona Skelton, Cleo Hehn and Myrna Yoder, started by painting the ceiling, seventeen feet up, with stars in varying shades of blacklight paint, so the whole room reads as a nightscape lit from above, fitting for a musician whose life was largely lived after dark.
The only clue McMenamins gives to find the room is that it isn’t always open, so you need to keep an eye on the operating hours of the smaller bars nearby to work out your window. It’s the strangest scavenger hunt I’ve ever half-heartedly attempted with a glass of wine in hand. And even then, I found it more by luck than design, which feels appropriate for a room dedicated to a man whose whole career ran on improvisation.
Family amenities at McMenamins Kennedy School
Kennedy School Theater © McMenamins
Families will love this hotel because it’s an utterly unique proposition and welcoming to every member of your crew. It isn’t one bar; it’s several, each with its own name, its own hours and its own personality, which means the grown-up guests can genuinely wander from one to the next on a hotel pub crawl of sorts, while the kids are off doing something entirely different two hallways over.
Soaking Pool © McMenamins
Whether that’s soaking in a heated pool tiled in colourful ceramics, built where the old teachers’ lounge once stood… or watching a film in the movie theatre in the old auditorium (now stuffed with couches instead of hard little chairs). Somewhere in between there’s a gymnasium hosting live music and events instead of dodgeball and a restaurant that spills out into a proper courtyard where the old cafeteria used to be.
The rooms keep the bit going too. The guestrooms in the main building are genuinely former classrooms, chalkboards and cloakrooms still intact, which delights kids in a way that’s frankly a little insulting to modern whiteboards. The newer English Wing rooms sit in the courtyard with literary themes instead, so you can choose between sleeping in an old classroom or somewhere inspired by a book or author.
Is McMenamins Kennedy School worth staying at?
Kennedy School Room © McMenamins
Absolutely! Especially if you like your hotels with a bit of personality. You can sleep in a former classroom, wander the old school corridors, drink in the old janitor’s room, soak in the pool and spend half the night discovering bits of artwork you somehow missed five minutes earlier. Where else can you check into a hotel and still feel like you might get caught out of bed after lights-out?
It’s not sleek, polished hotel luxury and that’s rather the point. McMenamins Kennedy School is weird, warm and wonderfully lived-in, with enough history and little surprises to keep you poking around lfor your enture stay.
What to know before you go
Kennedy School Restaurant © McMenamins
The Kennedy School is the kind of hotel where it pays to arrive with a little time to spare. The building is big, the bars have different opening hours and the Testimony Secret Room isn’t always open, so don’t assume you’ll be able to tick everything off in one lap.
If you’re staying overnight, I’d also book a room for the experience rather than expecting conventional hotel luxury. The rooms are full of character, the corridors aren’t exactly minimalist and the whole place is designed for wandering, drinking, eating and poking your nose into things you probably weren’t looking for.
And wear sensible shoes. You’ll do a surprising amount of wandering around this place and, if you’re like me, you’ll end up wandering half a kilometre looking for the secret bar you were sitting approximately 10 metres from for the previous hour.
History lessons
I came for the art and left thinking mostly about the people who wouldn’t let a tired old building quietly become a car park. I came away thinking about how easily this could have been a very different story. Every glowing mural and every stone-cold stove in this place exists because a neighbourhood decided their school was worth an argument.
More than four decades later, I got to get sozzled at school, on a school night, and get away with it. I did not get detention, though I did enjoy a quiet ale in the room that used to hand it out. That’s got to be worth an A+
McMenamins Kennedy School
5736 NE 33rd Ave, Portland,
OR 97211.
Ph: (503) 249-3983.
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An award-winning travel writer and photographer, Aleney de Winter was fresh from school when she first set off to explore the far reaches of Australia with a two-man tent and a beaten-up Kingswood for company. Three decades, and two kids later, and she's still on the go, with her itchy-footed offspring in tow. 