We stayed here on the last night of our trip to Portland, OR. The McMenamins compounds are basically the same across OR and WA, with the same food menus, same beers, and same drink menus. (McMenamins makes their own beer and spirits, and uses some of their alcoholic beverages in their mixed drinks.)
The Kennedy School was literally an elementary school back in its day, and the hotel rooms in the original wing are literally the classrooms! We stayed in the new wing, which is a recent addition that was so new it still smelled of fresh paint (not a complaint)! The Kennedy School compound is an artist's dream, as there is something to see everywhere you look. Artistic details range from mixed and matched antique lighting fixtures with amber bulbs, (the amber lighting is a blessing after a night of drinking at the compound), faux painted walls, hand painted scenery and borders, framed photos of the school back when it was actually a school, and art collages, among other creative details to the pubs and restaurants. You can spend an hour or more walking the halls and checking out the artwork, various pubs, and activity rooms. Within the compound are several pubs, a brewery, a main restaurant, a salt water soaking pool, a movie theatre, and places for live music.
Our favorite pub for design style was the Boiler Room, which looks like a steam punk fantasy, but it was very crowded, so we opted for the Honors Bar, which is tiny room, with a pot belly stove in the center, and only plays opera music. We also ate in the main restaurant by sitting at the bar, which is first come, first served. The wait for a table was over an hour, but we got a bar seat within 10 minutes by sheer luck. The food is basic pub food, and not at all greasy. Our favorite item was the Tater Tots, which are light and crispy, and can be ordered in any of the bars as an appetizer! The mixed drinks are fun to try, and they are not strong.
BRING YOUR SWIMSUIT for the soaking pool, and be prepared for it to be crowded. The salty water is therapeutic and worth braving the crowd. Don't worry about being seen in a swimsuit, as the lighting is dim, and all shapes, sizes, and ages are in the pool, and nobody cares what you look like so long as your "parts" are all covered! Also take the minimum amount of stuff with you to the pool, and wear flip flops. When we were there lockers were all full, so we hung our stuff on the fence, and some of it got wet.
We went through the compound in one night, and it was enough for us to get the full experience and have a lot of fun. If I lived locally I'd come here to use the pool, or to see a movie, or hear live music. The movie theater uses old couches strung together as the seating. There was not any live music playing the night we were there, but it would be fun to see a live show here. All in all, this place has a post college party scene feel, and young couples do bring their children with them to enjoy it.