So maybe spending the night in your classroom wasn’t exactly a childhood dream, but how about drinking cocktails in the auditorium, smoking cigars in the detention room, playing pool in the boiler room, or even brewing beer on school grounds? When the local McMenamins company, known for revitalizing historic Oregon buildings, took over the former Kennedy School—a 1915 schoolhouse recognized on the National Register of Historic Places for its distinctive architecture—the plan was to make school fun. And they did. The Kennedy School is now one of the coolest spots in Portland (though it’s a good 20-minute drive from downtown), complete with four trendy bars that attract a hip local crowd, a low-key gastropub with regular live music in the courtyard, a popular movie theater, an open-to-the-public soaking pool, and a brewery. Classrooms have been transformed into spacious rooms, with the kind of solid wooden furnishings and oversized, literature-themed artwork that inspire you to curl up with a good book—which would be seriously tempting if there weren’t so many other things to do.
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The Kennedy School may be a good 20-minute drive (or 40-minute trip on public transit) from downtown Portland, but it’s just a few blocks from the main drag of the Alberta Arts District, putting it firmly within the bounds of one of Northeast Portland’s quirkiest, most low-key neighborhoods. While the Kennedy School itself is a popular hangout for locals, Alberta Street offers plenty of other entertainment, including its renowned Last Thursday street party and art walk (held on the last Thursday of each month, as the name suggests). Favorite local spots include the Branch Whiskey Bar, Aviary, and an outpost of the cult-favorite Salt and Straw ice cream shop.
Need to Know
Rooms: 57 rooms. From $145. Check-in: 3 p.m.; check-out: 11 a.m. Dining options: The school’s onetime cafeteria has been converted into the lively Courtyard Restaurant, a quirky gastropub that serves breakfast, lunch, and dinner amid its mahogany booths and colorful pendant lamps—and, in warmer months, in the lush outdoor courtyard, which even has fire pits and a mosaicked fireplace for cool Portland evenings. The hotel also has four bars, each named for the converted room’s former purpose; for example, the boiler room is now the two-story Boiler Room bar, while the detention room has become the speakeasy-style Detention bar. The movie theater has its own bar and restaurant, too. All the bars and restaurants serve beers brewed in the on-site Concordia Brewery, and all bars offer light bites and bar snacks. Spa and gym details: While the hotel has neither a spa nor a gym, it does have a ceramic-tiled soaking pool in a secluded outdoor courtyard that was the teachers’ lounge. It’s free for guests and open to the public for a small fee.
Who's it best for: Book lovers and other experiential travelers looking for something out of the ordinary. Our favorite rooms: Rooms in the main school are all in converted former classrooms—complete with the original chalkboards—while rooms in the newer English Wing are each themed to a different iconic work of literature. If you opt for a room in the main building, be sure to get one of the king rooms with high ceilings and almost-floor-to-ceiling windows. In-house highlight: The Kennedy School is also home to a popular movie theater, which screens second-run feature films and favorite classics—and guests of the hotel get free admission!