McMenamins Kennedy School

McMenamins Kennedy School is the most Portland hotel in Portland, and for many visitors it is the stay they remember longest. The Kennedy School opened in 1915 as an elementary school in Northeast Portland, closed in the 1970s, and was rescued from demolition by the McMenamin brothers, whose company has turned historic buildings across Oregon and Washington into brewpubs, hotels and music venues full of art and whimsy. Here, the 57 guest rooms occupy former classrooms, many retaining their original chalkboards and cloakrooms, and each has a private bathroom; some rooms are themed around authors, and the English Wing, in the courtyard, has literature-inspired rooms. The building's hallways are covered in colorful murals and artwork that tell stories of the school, the neighborhood and the McMenamins imagination, and exploring them is part of the fun. Overnight guests get free use of the soaking pool, a warm outdoor pool set in a tiled courtyard (day visitors pay a small fee), and free admission to the Kennedy School Theater, a cinema in the old auditorium where you watch films from sofas and armchairs with food and drinks. The Courtyard Restaurant serves pub food in the former cafeteria, and a cluster of small bars — the Detention Bar, the Honors Bar, the Boiler Room and the Cypress Room — offer house-brewed beers from the on-site Concordia Brewery, cocktails and the McMenamins spirits. The school sits at 5736 NE 33rd Avenue in a residential neighborhood near the Alberta Arts District, about fifteen to twenty minutes by car from downtown. Trade-offs: rooms are simple rather than luxurious, the English Wing has no elevator or ADA rooms, and you will want a car, transit or rideshare for downtown sightseeing.

Staying at Kennedy School feels like a sleepover in a playful museum. Evenings are the highlight: a soak in the warm pool, dinner in the Courtyard Restaurant, a movie in the theater with a beer in hand, and a nightcap in the Detention Bar, with its classroom-punishment theme. The building is also a neighborhood gathering place, so expect locals in the restaurant and bars, especially on weekends, and occasional live music and community events. Look for the newest art, including a secret-room mural completed in late 2025.

The location is a plus for travelers who want to see residential Portland. The Alberta Arts District, with its galleries, shops, cafés and the Last Thursday street fair in summer, is a short walk or bike ride away, and the neighborhoods of Northeast Portland have some of the city's best casual restaurants. Downtown and the main sights are reachable by bus, rideshare or a short drive; the airport is about fifteen to twenty minutes away, making it a convenient first or last night.

Kennedy School suits couples looking for something different, families who will love the theater and pool, beer lovers, and anyone who appreciates quirky, history-filled hotels. It is not for travelers who want sleek luxury or to walk to downtown sights. Book early for weekends, and request a classroom room if you want the full chalkboard experience. The gift shop sells McMenamins souvenirs, beers and spirits, and the company's other properties in the region, including Edgefield near the Columbia River Gorge, make good companion stays for travelers who fall for the style.