- Go with a group of awesome friends who never stop bringing the fun.
- Voodoo donuts: hit it up around 1-2am. Any other time and there will be a 2 hour lineup.
- Wander with no agenda! You may discover that the Pearl District has an art walk full of kind-of-pretty-good and the occasionally really good artwork.
- Get your tarot cards read at the Saturday Market (also in the Pearl District). You will leave feeling incredibly hopeful about your future.
- Powell's Books. Just go. You will be amazed.
- Give yourself a challenge/game. Mine was to take pictures with all of the servers we encountered on the trip. We had another game of taking photos with the local hipsters without them realizing it, but never actually did it. Fun fact: there aren't as many hipsters in Portland as one might expect. Or we were too mainstream to be in their neighbourhoods - we did see the most on Alberta St if you're looking.
- Eat eat eat. Restaurants we visited included The Clyde Commons (gourmet-esque food for non-gourmet prices!), The Tin Shed (breakfast! adorable lady-server!), and Daschutes Brew Pub (best grilled cheese ever! really cute male server!).
- Drink drink drink. Find that pub we found on Alberta Street that has ping pong tables and Apples to Apples in their backyard area. Or that other pub that also has a great backyard area. I say backyard area because it actually feels like you're in your friend's Mom's awesome backyard and not a fancy patio. Also, find that bar that has a bowling alley.
- Don't go to the club your cute server from Daschutes recommended. It looks lame.
- Talk to the locals! Everyone is so nice, especially if you're a gaggle of attractive, cool ladies from The Real Vancouver.
- If you're wandering around and see a sign for a yard sale, go check it out. The people holding the sale could very well be a group of Vaudeville performers with an amazing double-decker bus they use as a dressing room and stage-backdrop and they will let you walk around the bus and take pictures. They will also have a toy horse covered in mirrors andwill recommend a vintage shop up the street you wouldn't have found where you will buy the cowboy boots you've always wanted for $14, which is next to the other vintage shop where your friend will get the sexiest Betsey Johnson heels of all time for an equally great price that you will forget.
- Leave good tips. Apparently they think Canadians are bad tippers there. Let's work together to change that!
- Pick a neighbourhood and spend the day there. We did The Pearl on day 1, Alberta/Mississippi on day 2, and then Nordstrom's in the morning of day 3 before hitting the road.
- The Doug Fir also has attractive wait staff and cheap concerts.
- Use Radio Cabs for all your cabbing needs - their drivers are also attractive and have great senses of humour.
- FOOD CARTS! Go to them all. Especially Brunch Box with their grilled PB&J shaped like a dinosaur. Don't worry, you don't even need to look for the food carts, they will find you.
- Are you rocking the diet-restricted life? Never fear! Every single restaurant has dairy, gluten, and animal-product free options and the servers will be happy to indulge your every request.
- Get ready to admire the hugely attractive local population - everyone in Portland is beautiful!
So you're going to Portland?
Wondering what you should do on your next trip to Portland? Take a tip from me!