For the upcoming weekend? Given that it's Rose Festival, recommendations may vary. Downtown will be very crowded and traveling across the city could be very difficult.
The
Rose Festival and its associated events are always worth attending. I love the Dragon Boat Races, in particular.
Some excellent recommendations for restaurants in various categories can be found
here. Check out the
foodcarts. Have a
Voodoo donut.
As for "sights" to see, a lot depends on your interests: visit the
Rose Garden,
Classical Chinese Garden, the
Japanese Gardens, the
Rhododendron Gardens,
Leach Botanical Gardens. The
Historical Society has nice exhibits, and the
Art Museum is small, but has a nice collection. Or visit one of the offbeat,
small museums.
If you're a reader, a visit to
Powells is a must. Ride the
Tram, stroll the neighborhoods:
Hawthorne with its mix of stores,
Sellwood with its antiques, the trendy shops and restaurants along
NW 23rd, the "hip"
Pearl.