This post was originally published on A Globe Well Travelled in 2016. The content has been revised and updated with fresh information.
Ahh, Portland. The Oregonian city that holds such a special place in my heart.
I’ve visited Portland twice. The first time, Rob and I were doing a road trip up the Pacific coast and we stopped in for a few days to check out whether the city is actually as cool as everyone says it is (can confirm: it is very cool).
I liked Portland so much that I went back again to explore the city some more. After my second visit, I made the claim that Portland is my favourite city in USA, and that claim still stands. Here’s my recommendations on the best activities for a weekend in Portland, Oregon!
Where to stay in Portland, OR:
On our first trip to Portland we stayed at the Downtown Value Inn, which was very basic but the location was great – we could walk to Pioneer Courthouse Square in under 10 minutes.
My second trip was based at Eastside Lodge which I liked slightly better. The location was a tad further away, but there were frequent buses going by on Burnside St that got me into the city in 10 minutes.
The best things to do in Portland, Oregon
1. Wander through downtown
Downtown Portland is actually a really nice area to walk around. Unlike many other cities in the US, the streets are optimised for pedestrians, cyclists, and trams, so you don’t feel as though you’re looking over your shoulder for cars all the time.
Pioneer Courthouse Square (pictured above) acts as the center of downtown, and is a lovely area to chill and people-watch for a bit. From there, you can walk along SW Broadway to see the iconic Arlene Schnitzer Concert Hall, then head down to SW 5th Ave to see the famous Portlandia statue.
Walk north along waterfront park until you get to Burnside Bridge. To your left is old town, which is where you’ll find the White Stag sign, the Keep Portland Weird mural, and the super cute SW Ankeny Street with all its bars and restaurants.
2. Walk across the bridges
The Willamette River runs through the center of Portland, dividing the city into west and east. Portland has 12 bridges crossing the river, each with a unique style and structure.
9 of these bridges are close to downtown, so put on some comfy shoes and take your pick of bridge to walk across! I chose Burnside Bridge and Hawthorne Bridge, both of which offered fabulous views of the city skyline.
3. Sample some craft beer
Oregon has an exceptional number of brewing companies. Every pub serves a different local brew; you could quite easily try a new beer every day of the year if you wanted to. A few breweries you could try are Breakside Brewery or Hopworks Urban Brewery. You can do these breweries on your own or through a Portland breweries bike tour.
Portland also has two festivals dedicated to the love of beer, the Oregon Brewfest and the Portland Craft Beer Festival. You can attend either (or both) of these events in July and taste every craft brew in the surrounding states.
4. Hop into the pubs and bars
You’re guaranteed to find some weird and wonderful pubs and bars in Portland. Here are some of my faves:
McMenamins are known for having their drinking holes inside old buildings that were never meant to be pubs. You can have a pint in a classroom at Kennedy School, drink beer with a movie at Bagdad Theatre, or have a beverage in a historic hotel at Crystal Ballroom.
If arcade games are your thing, then try drinking at Ground Kontrol. Here you can play Pacman with a beer in hand, and watch the other patrons play Rock Band with the screen projected on the side wall.
5. Consume donuts
Portland is actually one of the best places in USA to consume gourmet donuts! If you’re truly a donut fanatic, you can even do a Portland coffee and donut tour.
There are two stand out places to consume donuts in the city. Voodoo Doughnut is the most famous, especially its downtown location which can get insanely busy, but if you want to sample the donuts without having to line up for ages then there’s a Voodoo Doughnut 2 on the east side.
You definitely have to try the signature Voodoo Doll (pictured above), and maybe some of the other crazy donuts such as the Tex-Ass Challenge (6X bigger than other donuts), the Cock-N-Balls (shaped appropriately and filled with cream), and the Gay Bar (cream-filled with rainbow fruit loops).
The other donut shop that is contested as the best in Portland is Blue Star Donuts. Where Voodoo goes with delicious fatty wackyness, Blue Star goes for superb quality with it’s French recipe and super Instagrammable flavours. Try the Piña Colada, Passionfruit Cocoa Nib, or the Blueberry Bourbon Basil.
6. Go vintage shopping in Hawthorne
If you’re like me and enjoy spending time in hipster neighborhoods, then you’ll love Hawthorne. This area is packed with vintage stores, antiques, boutiques, quirky eateries, and some killer street art.
Start by heading to Buffalo Exchange (only the most amazing thrift store ever), and walk along SE Hawthorne Blvd in either direction to explore the area.
7. Get your coffee fix
There’s no denying that Portland is one of the best cities in the US for coffee snobs. Here you’ll be able to walk into any cafe and grab a damn good cup of joe.
Start by sampling the roast at Stumptown Coffee. These guys have numerous locations all over the city and have made a name for themselves by perfecting the brewing process from start to finish, and by having a truly exceptional cold brew.
8. Visit some of the gardens
The Lan Su Chinese Garden in downtown is surprisingly quiet and absolutely beautiful; I spent a good hour just sitting around and admiring the lily pond, quaint bridges, and Chinese-style buildings.
Head up to Washington Park and you’ll find the International Rose Test Garden where you can see what seems like every type of rose in existence. Across the road you’ll find the Japanese Garden (pictured above), which is a rather large and extremely pretty place to explore.
9. Check out Pittock Mansion
My reason for visiting Pittock Mansion was mostly for the city views, but I was pleasantly surprised to find that the museum itself was an interesting insight into local history.
The mansion was built in 1914 for one of Portland’s most influential families. The house was abandoned in 1958 and badly damaged in a storm in 1962. The people of Portland came together in 1964 to save it, repair it, and turn it into a museum.
10. Eat at one of the food carts
Never have I been to a city with such amazing street food. Portland has over 500 food carts serving an insane variety of cuisines. Want some Georgian, Columbian, or Ecuadorian food? No problem! One of the food carts is sure to have it.
You’ll find the largest selection of food carts at the Alder St. Food Cart Pod, which lines a parking lot at SW 9th Ave and Alder St.