Oregon, USA

My top picks for Portland, Oregon

I was intrigued to visit Portland after working alongside a Portlander in Hawaii – she’d told me stories of vegan strip clubs (girls weren’t allowed to wear anything made from animals and only vegan food was served), their relaxed drug laws and the fact they don’t have any state tax on their items.

While I only participated in one out of these three things (you pick which one…), I did in fact do and see quite a few other things in this “weird” city and thought I would share my top picks!

Full disclosure: I was REALLY sick when I was in Portland – I had been traveling and not eating enough vegetables for about three weeks at this point and my body was punishing me. I still tried to explore as much as I could every day but I definitely need to go back and do more.

  1. Visit the famous Voodoo Doughnuts

I’d heard about this place from about a million people before even getting to Portland so naturally it was number one on my list. I was lucky enough to not have to wait in a line but I’ve heard the line can get pretty hectic so make sure you allow for this! In all honesty, I thought their donuts were just okay – nothing to write home about but also not awful. I actually preferred Blue Star Donuts which I’ll mention in another point too.

“Good things come in pink boxes”
  1. Stay at HI USA Hostel and do the free walking tour

Another great hostel with two locations in Portland – I stayed at the HI NorthWest Hostel as it was closer to downtown (20mins walk). I stayed at a few HI hostels across America and they were always great (see my hostel blog post here). This one was particularly good as they offered a free walking tour of the city and I found out lots of things I wouldn’t have known otherwise like the Zoobomb tradition every week (google it, so cool!).

  1. Get lost in the largest independent bookstore in the world

Powell’s bookstore is so large, it takes up an entire block in downtown Portland! I have to admit, it was quite overwhelming for me and I didn’t know where to start so I wandered aimlessly looking at a few things before giving up. If you know what you’re after, this bookstore would be heaven. If you’re like me and will read anything that looks somewhat interesting, I’d give yourself at least three hours to explore this haven.

  1. Visit a brewery (or ten) and try the local drop

It’s well known that Portland is famous for their breweries and craft beer so when in Rome right? As I was quite sick when I was here, I only tried a couple of local beers, but that just means I have to go back to try more yeah?!

  1. Head to Nob Hill area and stroll down NW 23rd Ave

One of the cutest little streets, perfect for window shopping, with adorable cafes and home to a number of famous eateries such as Blue Star Donuts (make sure you try the key lime and lemon one) and Salt and Straw.

  1. Find a friend or friends friend or friends cousin (or anyone you can) who works at the Nike Headquarters and get a pass to go visit

I found out Nike has their HQ in Portland only when I got there and was so excited to check it out! After catching two different trains and making my way to the reception, I come to find out you can only go in if you have a pass from someone who works there – not even my charming accent could sway them. Sigh. So before you head out there, ask around and get yourself a pass and let me know what it’s like inside!

  1. Find the smallest park in the world

Another fun fact I found out from the free walking tour; in downtown Portland you can find the world’s smallest park, Mills End Park. I wouldn’t exactly call it a park but each to their own…

Blink and you miss it!
  1. Don’t go to the Freaky But True Museum

Just don’t. Not worth it.

  1. Hike up to Pittock Mansion and explore Kerry Park

Even though I was super sick while in Portland, I didn’t want to completely waste my time while there. I made sure I left the hostel at least once a day for a couple hours and for some reason, the day I was feeling the absolute worst, I decided to hike up to Pittock Mansion and also explore nearby Kerry Park. Both were beautiful with great views over the city but definitely a lot of distance – I ended up walking 18kms this day!

  1. Shop up a storm at a Nike Factory store

Super cheap Nike gear – need I say more?!

  1. Visit Hunnymilk for a delicious brunch

I continued my quest to find the best brunch spot in each city I visited and in Portland, that place was Hunnymilk! One sweet option, one savory option and a drink for only $20 (and no sales tax!). I got the caramel hot chocolate with roasted marshmallows, the brunch quesadilla with a refried bean fritter, and the vanilla bean French toast. Oh my lordy it was good.

Mmm, I really want this all over again
  1. Check out the Saturday market

Portland boasts the largest continuously operated outdoor market in the USA and it is pretty impressive. Head down to the waterfront just past downtown on a Saturday morning and you’re sure to find it.

  1. See the Swift phenomenon at Chapman Elementary School

If you happen to find yourself in Portland during the month of September, make sure you head to Chapman Elementary School an hour before sunset to see thousands upon thousands of swifts heading into the chimney to sleep for the night. It is as weird as it sounds but honestly one of the top “wow” moments on my travels.

  1. Find all the Simpsons street names

As a HUGE Simpsons fan, I left my favorite point for last. There’s an area in the NorthWest called “the Alphabet district” where the streets start at “A Street” and go right down to “Z Street”. And if you’re eagle-eyed, you’ll notice familiar names on these streets from the Simpsons show. Matt Groening, creator of the Simpsons, was born in Portland and named a lot of the characters on areas around the city. For example: Groening grew up on Evergreen Terrace, Montgomery Park can be found on Burnside Street, and you might see Flanders Street, Kearney Street, Lovejoy Street, Quimby Street, and Van Houten Avenue on your explorations. Bonus fun fact: Groenings parents are called Homer and Marge, his sisters Lisa, Maggie and Patty.

Keep your eye on the street signs for some familiar names

Well that concludes all my top tips for Portland, Oregon. Let me know in the comments below if I have forgotten something or if you agree with any of my points!

Courtney xo

P.s. Keep Portland Weird 😉


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