10 essential activities for a weekend in Portland

10 essential activities for a weekend in Portland, Oregon

Ahh, Portland. The Oregonian city that holds such a special place in my heart.

I’ve visited Portland twice. The first time, Robert 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 was actually as cool as everyone said it was (can confirm: it was).

I liked Portland so much that I included it as one of 5 cities I’d go back to in a heartbeat, and then I actually did go back again (though 2 years later was quite a lot longer than a heartbeat). Last year I attended a conference in Portland, and was reminded just how much I love the city.

After my second visit, I made the claim that Portland is my favourite city in USA, and that claim still stands. A friend of mine recently asked me why I didn’t have a city guide to Portland on the blog, so I figured it’s about time to put together my recommendations for a weekend in Portland, Oregon!

Keep Portland Weird sign

Where we stayed:

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.

Pioneer Courthouse Square, Portland

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.

Portland, Oregon

2. Walk across the bridges

The Willamette River runs through the center of Portland, dividing the city into its west and east sides. 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.

Craft Beer, Portland Oregon

3. Sample some craft beer

Oregon has 194 brewing companies, 61 of which are in Portland. Every pub serves a different local brew; you could quite easily try a new beer every day of the year if you wanted to. 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.

My fave brewery from my last Portland trip was Base Camp Brewing Company on the East Side. A few others you could try are Bailey’s Taproom, Breakside Brewery, or Hopworks Urban Brewery.

Bars in Portland, Oregon

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.

Voodoo Doughnut, Portland

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.

Hawthorne, Portland, Oregon

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.

You could also grab a cup at Heart Coffee Roasters on the east side, or Coava Coffee in Hawthorne.

Japanese Garden, Portland

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.

Pittock Mansion, Portland

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.

Portland food carts

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. You can find a map of all the food carts in Portland here.

You might also like:

16 Responses to “10 essential activities for a weekend in Portland”

  1. Lorna

    I remember really wanting to visit Portland after reading your post about why it’s your favourite US city – this has only increased my eagerness to visit one day! The doughnuts are the standout for me in terms of what I’d look forward to trying. They look insanely good.

    P.S. Just wanted to say how much I adore your blog. Having recently started a blog of my own, your site is the one I keep coming back to for awesome blogging/social media tips (as well as inspiring travel posts, of course). I’ll stop gushing now, but thank you so much for providing such consistently brilliant content. 🙂

    • Ashlea Wheeler

      The doughnuts are truly awesome! I’m sure you would love Portland, I hope you get the opportunity to visit the city sometime soon.

      And thank you for your wonderful comment, Lorna! It’s so nice to hear such positive feedback about my blog 😀

  2. Maria

    Portland sounds like the coolest city ever! I have never been but I desperately want to go now 😀

    • Ashlea Wheeler

      It seriously is! Everything about Portland is both weird and wonderful 😀 You should definitely plan a trip, Maria!

  3. Paris

    I’m glad I came across this post. I’m heading to Portland very soon.

    • Ashlea Wheeler

      That’s great news, Paris! I’m sure you will love Portland 😀 Let me know what you thought of it after your trip!

      • Paris Jones

        Back from my visit to Portland. I really enjoyed my time out there. I visited some of the places you mentioned like Pioneer Courthouse Square, Ground Kontrol, and Lan Su Chinese Garden. Stumptown Coffee is best. So were the food trucks. And I can see why everybody is crazy over Voodoo Doughnuts. They’re so good. I even saw someone at the airport about to board a flight with a box of them when I was heading back home. Overall, I like the laid back vibe of the city and look forward to visiting again sometime in the future.

        • Ashlea Wheeler

          I’m so glad you had a good time in Portland! How great are the food trucks, and the coffee, and the doughnuts 😀 Portland really is a foodie’s dream. Thanks for sharing your experience of the city with us, Paris!

        • Kate

          Hi Paris. Where did you stay? Did you rent a car? What can you add to Ashlea’s blog ?

  4. Michele

    You forgot to mention Powell’s Book Store – don’t miss this store on Burnside, downtown Portland!

    • Ashlea Wheeler

      Powell’s is wonderful! I didn’t include it in this list as I don’t think it’s really a ‘must see’, but it is a great place to check out if you’re a book lover 🙂

  5. Kate

    Thank you Ashlea, I’m headed to Portland in October for the first time!

    • Ashlea Wheeler

      That’s so exciting, Kate! I’m sure you will love Portland 😀

  6. Jenni

    Live just north of Portland, actually going there tomorrow for a night out with friends. March is Portland dining month. I love visiting and walking through Portland. We visit whats refered to the west side primarily. Glad you were able to enjoy the city.

  7. Sharla

    Heading to Portland next week for the first time and I’m SO excited to see that our itinerary holds most of the things on your list! We will never make it to all of the restaurants on my list so what are some of your favorites?

    • Ashlea Wheeler

      That’s so exciting, Sharla! I’m glad that you’re already planning on seeing most of these places in Portland. I think Elephant Deli was my fave food place 😉


Leave a Reply

Basic HTML is allowed. Your email address will not be published.

Subscribe to this comment feed via RSS