McMenamins Kennedy School. Photo by Sarah Yeoman

A Hospitality Crash Course With Portland’s Kennedy School Hotel

BY Sarah Yeoman | April 17, 2024

This story was first published in The Hotels issue (#6) which hit stands in March 2024. McMenamins Kennedy School was one of the hotels named to our first-ever Greatest Hotels Ever list.

The McMenamins company is, in a way, quintessential Portland. It’s at the same time peculiar and charming, eccentric and unique. The eclectic chain of family-owned businesses has a strategy that seems to be guided by only investing in cool places where people will want to hang. These include breweries and music venues, theater pubs and hotels. They’ve transformed hollowed-out buildings into hotel and dining experiences since its first pub opened in downtown Portland in 1985, just as the country began to embrace the new idea of boutique hotels in the early ’80s. 

Kennedy School Hotel exterior. Photo by Sarah Yeoman.

Having now expanded to 12 hotels and dozens of pubs throughout the Pacific Northwest, each property is infused with a fanciful ambiance that’s become McMenamins’ signature style and keeps each spot feeling unique. Most of the hotel locations are historic buildings, like Masonic lodges and elementary schools. The Kennedy School hotel was the latter from 1915-1975. After its final bell rang, the school sat for decades, vacant and crumbling. Then McMenamins got their hands on it in 1997 and transformed it into a neighborhood staple in tree-lined Northeast Portland. But they didn’t just gut the place to the studs and throw in the trendiest decor. No, Kennedy School draws visitors into its hallways with a combination of historic charm and artistic whimsy. Filled with unusual hand-painted art and historic photos of pupils and teachers of past generations, the original classrooms, signs and fixtures let you know this was a functioning school — like the comically small water fountains that were obviously designed for children over a century ago.

In the school wing of the hotel, each room is a former classroom named for a teacher, student or employee of Kennedy Elementary School when it was in operation. More original artwork spans the walls (and sometimes the headboards), vintage lamps and furniture decorate the spaces, and many rooms also feature original school chalkboards.The English wing is a hotel addition in the courtyard with rooms sporting literary themes. But whether you stay in the historic rooms or the newer spaces, you are guaranteed to be immersed in the school’s story.

Kennedy School soaking pool. Photo by Sarah Yeoman.

Where Kennedy School really shines is its labyrinth-like network of wandering hallways connecting four bars, a soaking pool, movie theater, brewery, restaurant and gift shop. On any given weekend you’ll find tourists and locals catching a flick in the sofa-stuffed movie theater or bouncing from bar to bar. It’s quite easy to spend hours relaxing in the saltwater soaking pool, enjoying a meal and partaking of Kennedy School’s drink selection featuring concoctions unique to each bar (my husband and I did just that when we chanced upon Kennedy School on our first visit to Portland almost 10 years ago).

The bars are experiences in themselves. Starting at the mellow Cyprus Room, grab a rum-based cocktail and lounge among balmy plants and artsy light fixtures while a reggae soundtrack bounces in the background. On non-rainy days (more common than you might think in Portland!), the patio opens up for an extra-laid-back vibe.

Kennedy School’s Detention Room Bar. Photo by Sarah Yeoman.

Don’t worry about finishing your drink before moving on to the next stop — you can bring your drink of choice along while touring the rest of the school. Squeeze into the microscopic Honors Bar for a dose of opera and a premium cocktail or rummage up some mischief in the tiny Detention Bar, with its high walls, tapestries and a nice selection of whiskey.

While both Honors and Detention bars were janitor rooms complete with wood-burning stoves to keep you toasty, the Detention Bar was also a cigar lounge for the first few decades of Kennedy School’s revival. (You can still get a solid stogie here, but you’ll have to enjoy your smoke outside.) 

Kennedy School’s Boiler Room bar. Photo by Sarah Yeoman.

The Kennedy School’s Boiler Room is the most epic drinking spot. Located in the original boiler room of the school, it’s a spectacular sight of iron, artwork and ambiance. Created by McMenamins’ plumber, a maze of intricate pipework stands in for traditional handrails as you make your way downstairs to order a drink — hold on tight, there’s a lot to marvel at. See if you can spot the doors from the original boiler that provided heat for students in the winter, on display near the upstairs pool table. 

Beyond the bra crawl, there’s plenty more to explore. The Courtyard restaurant (formerly the cafeteria) is where you can find pub food and mahogany booths; the heated soaking pool (formerly the teacher’s lounge) is never a bad idea, and is included in an overnight stay; if it’s open, definitely take a tour of the on-site brewery (formerly the girls lavatory), or catch one of the music events that take place in the gymnasium. There’s more, too. 

Kennedy School Courtyard Restaurant. Photo by Sarah Yeoman.

While hotels around the country have leaned into the boutique business, attracting travelers with one-of-a-kind designs, dining options and local experiences, what Kennedy School has achieved is they’ve not only curated a destination for visitors, but one that attracts locals, too. As someone who has experienced the school-turned-multi-purpose-specialty-hotel as both a tourist and a Portland transplant, the place holds up well, visit after visit.

Lastly, a highly recommended tip: If you’re a local or visit the Pacific Northwest frequently, the McMenamins Passport program is a great way to explore the region via the properties throughout Oregon and Washington. After my husband and I moved to Oregon without knowing a single soul, we picked up the passports as a way to get to know our new home. The basic gist is to collect stamps from each venue — hotels and larger properties have multiple stamps — and receive prizes once each leg is completed. Finish the whole book and you’ll claim the crown of Cosmic Tripster, which entitles you to free hotel stays, concert tickets and a special party exclusively for those high-achieving passport fillers. But collecting stamps involves more than just walking up to the front desk. You’ll be sent on a scavenger hunt unique to each property. Getting all seven stamps for Kennedy School can take awhile — which is a perfect setup to enhance your classroom experience.