Hotel: Hands down, no doubt about it, you must stay at the Kennedy School. It's a bit out of town but, if you're only staying for a weekend, you won't even notice the distance. Get there on a Friday late afternoon, check-in, and plan to spend the whole night there; you can check out the rest of Portland tomorrow. Kennedy School has restaurants and bars on site (yes, plural of both), entertainment including pool tables and a cinema, a lovely soaking pool (which we weren't prepared for but, especially after seeing it, wish we had been), and the ability to stroll the halls with a beer in your hand (like Vegas). It's a great hotel and a great destination and I only wish we'd been able to experience it more than just once.
Restaurant: Pok Pok - this place is crowded all the time. Just accept it. Put your name on the list, go across the street to their bar (Whiskey Soda Lounge), have a drink until they call your name, and then go experience some amazing food. Done. Caution: someone might whip out a boob and start breastfeeding next to you whilst you're enjoying a drink and/or meal. No judgement, just providing you with some notice so you can mentally prepare for this possibility.
There's another restaurant that I'd recommend if I could remember anything about it beyond the amazing food and atmosphere. I remember we had to drive east from downtown, it was in a neighbourhood, and we sat outside in an amazing garden area. Otherwise, I have nothing else to help recall it's name or location. It was great, though.
Activity: I highly recommend the Worst Day of the Year bike ride. If you do the full ride you've got two killer hills but both are well worth the effort. I suggest taking the short cut after the second hill, which really should be the end anyway.
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