Getting around: The Max is very easy to use and goes everywhere. The Portland Street Car is awesome if you’re going SW to NW Portland and especially around the Pearl District. You can rent bikes all over the place and they have tons of Zip Cars. Uber and Lyft abound. I usually just park in one of the all-day garages and walk all around if the weather is nice.
The Pearl District is one of my favorite places to walk around for an afternoon. There’s also tons of little shops and food options on Alberta and Mississippi and it’s a very cool vibe. If you're over towards the waterfront you can hit VooDoo Donuts on your way to or from the Saturday Market, and there are tons of food carts around that area as well. (There's an alley behind VooDoo Donuts if you're walking towards the water, like, go out the door and take a left outside the doors, and there's a row of tiny little bars there. My friends and I often do our daytime pub crawl down that alley.) There are often events at the Waterfront Park right there – think beer fests, food fests, music fests. The best market IMO is the Farmer’s Market at PSU tho.
My fav neighborhood to pub crawl at night starts at Jakes’s Famous Crawfish, which has an awesome happy hour. Living Room Theaters is right around the corner and has unique movies, live music, reasonable food and drink prices. Ringler’s Annex is a cool downstairs bar on Stark, just a couple blocks from Jake’s. That whole neighborhood is awesome and on the weekends there's great people watching. The Crystal Ballroom is around the corner and they have great shows there.
If you’re into late night fun, there is a whole scene down towards the water with dance and strip clubs. They’re pretty fun if that’s your thing. They have pedi-cabs all around at night and if the weather is good, it can be a pretty raucous scene. (I just walk down there after a night out around the neighborhood above until you find a pedicab and tell them what you have in mind). Food carts all around there too for a late night snack. You can also set up pedicab tours to breweries and distilleries too.
The Doug Fir Lounge is a fab place to see live music.
Ground Kontrol is a cool arcade game place, with food and booze that’s fun to go play all your fav old school video games.
OMSI is a really cool museum and has an IMAX theater. I love the Portland Zoo.
Portland City Grill has a really good happy hour, and a cool mix of partiers and biz people (little dressier). Probably one of the best views in Portland IMO.
Ice cream at Salt and Straw is always a must.
Salty's on the Columbia has the best damn champagne buffet brunch I've ever seen outside of the Bellagio in Vegas. It's spendy af and you have to make reservations, but it's a spectacular spread and beautiful view (need a car to get there).
If you have good weather and want to get some nature in: Japanese Gardens, Washington Park, McMenemens Edgefield, Pittock Mansion (grounds are beautiful if the inside isn’t open). If you have a car, Multnomah Falls is a sight to see.
Shopping: If you have a car, the Woodburn Outlet Mall is about 30 mins south of Portland and has a ton of stores. I also love walking around the Pioneer Courthouse Square area as there are lots of shopping options there…a huge Nordstrom Rack, tons of shops in Pioneer Place Mall, tons of shops in a couple block radius. Take advantage of no sales tax!
Pro tips: it’s pronounced Or-E-Gun and Wi-lamb-it
Have fun!!!
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. Lots of other great stuff, though.
