Oregon's largest city, Portland has (and maintains) a reputation for a hippie/funky/artsy kinda culture. Nicknames include the Rose City and the City of Bridges.
Major Events: Portland Rose Festival, World Naked Bike Ride (yes, it's what it sounds like...no, I didn't go), and a slew of music and food festivals.
Nav:
International Rose Test Garden: Professionals come from all over the world each year to both plant new hybrid roses and to judge the best of the best. The Portland Japanese Garden is also nearby.
Downtown Walk or Uptown Drive: See the cool architecture and funky shops in the Old Town area or drive up through some of the hillside neighborhoods with million dollar views (homes up there can literally cost over $1 million).
Check out one of the many McMenamin's (a local institution for sure) locations, such as the one in the Edgefield neighborhood. They do their own distilling, brewing, farm to table cooking, run hotels, and spas, etc...
Lost Lake: Head east of town about two hours to toward Mt. Hood and visit Lost Lake for a day of swimming, kayaking, fishing, barbecuing, etc...
Nosh:
Salt and Straw: Ice cream shop with funky flavors like fried chicken, deviled egg, and spinach cake. For those looking for a more traditional cup or cone, they have cookie dough, chocolate, etc...
Portland City Grill On the 30th Floor: Happy hour and the views are legit. Sushi, bao buns, roasted cauliflower...a margarita and an old fashioned.
Nip:
Portland City Grill On the 30th Floor: An Old Fashioned and cucumber margarita. The Old Fashioned was kinda thin on the whiskey so maybe stick with the margarita.
