The 11 Best Ways to Spend Your Days in Portland, Oregon

Haylee Sandra
Apr 14, 2020
7 min read

I've loved Portland since the first time I spent a measly one day in the city 3 years ago. That day was simply not long enough to encompass all the amazing sights and activities this city has to offer. So, pre-pandemic, my husband and I flew up to the city for a few days as he had never been and I simply *needed* to explore more. And to no surprise, this city still captures my heart! If you are either planning a trip to Portland yourself, or you're looking for the perfect place for a getaway, keep in mind some of these must do's and see's while you're in the city of beer, donuts and weirdness!

1. Hiking

Portland (Oregon in general) is a great spot for outdoor enthusiasts and hikers alike. You have endless options for trails and scenic overlooks if you're trying to see as much nature as possible. In the winter time, snowshoeing around Mt. Hood is an incredible adventure. You also have to see the Columbia River Gorge, as it is stunning! This city itself is very environmentally friendly and nature-conscious, so you won't struggle to find outdoor activities or organized group hikes if you're looking to be social.

2. Multnomah Falls

An iconic waterfall you have to cross off your list is Multnomah Falls. Just 30 minutes out of the city, this waterfall is incredible! Standing over 600 feet tall, you'll be awe-inspired just taking it all in. It's one of the most famously instagrammed and photographed waterfalls for a reason! If you have your own car, you can easily drive and park there. But if you are flying into the city and without transportation, there's plenty of cheap tours that take groups to the waterfall, and they'll also make stops at other waterfalls and lookout points along the way.

3. Breweries, breweries, breweries!!

This city does not lack in beer. And if you know anything about Portland, you know how they are considered one of the beer capitals of the United States (if not the world!) and have endless options in the craft beer brewery department. My husband and I loveeee us some beer. Anson is a self-proclaimed beer connoisseur, if you will, so I knew Portland was just the city for him. We went to a lot of breweries in our few days. Some of my favorites include Breakside Brewery, Deschutes Brewery, Old Town Brewery, Bailey's Taproom and Lucky Labrador Brew Pub. BUT, don't stress yourself too much over picking which breweries to go to. A bad brewery in Portland just doesn't exist, in my opinion. It can't! Too much competition to stay booming in a brewery business in this city if you aren't of quality. Just pick ones with the best names and the ambiance you're looking for, exploring the best beer will follow.

4. Take advantage of the food pods and try a food tour!

Portland is known for many things as you can see already, but one of their most popular trends is the availability of food pods and food trucks all over the city. In fact, almost all of the actual restaurants in the city started out as a food truck, that would then upgrade into an actual restaurant if popularity took off. But how do you know where the best food pods and restaurants are? Well, my main recommendation would be to book a food tour!

Portland offers a wide range of tours, and Anson and I love food tours whenever we go to a new city. We believe that really diving into a region or a city's food is the best way to get to the bones of the culture of that particular city. We do one in almost every new city we explore abroad, but decided we needed to do one in Portland as well as food culture is a whole new scene here!

We booked a tour with Portland By Mouth Food Tours, and Sherri (the founder and guide) was amazing! She offers different tours throughout the city, and the one we booked was "The Bustling Buckman Hood - Hawthorne, the Goat Blocks and More" walking tour. On this tour we had 5 stops. The first was at a quaint Italian eatery called Nostrana, followed by an amazing Russian restaurant (it was our first time truly trying Russian food!) called Kachka (their horseradish vodka was fire!), then a Venezuelan restaurant named Teote. We then headed to a food pod where we had waffle sandwiches for dessert at a food truck called Smaaken, and finished at Jacobsen Salt Co. This tour was an all encompassing way to see several different places to eat in this district that we would have never discovered otherwise. In addition, Sherri was extremely helpful to us in planning out the rest of our days in the city, with several recommendations on brunch spots, breweries, and other types of cuisine we were looking for. I will include Sherri's booking info below so that you can reach out to her if you're in the city!

portlandbymouth.com

5. Portland Walking Tours

This is an especially great option for first-timers to the city. This company offers a variety of daily walking tours so you can pick which ones seem the most intriguing to you! Anson and I did both the "Best of Portland" walking tour and the "Underground Portland" walking tour. I think these two paired together were a fantastic way to really learn about the city, modern day and its history! It was also really fascinating to learn about the backstory of Portland's underground tunnel system and to debunk all the myths that are famously associated with them. If you'd like more information about this company and what tours they offer, follow the link below!

www.portlandwalkingtours.com

6. Catch a comedy show!

I loveeee comedy clubs! And unfortunately, I feel like they are a lost art! There's not enough cities that have comedy clubs anymore, so if I find that we wound up in a city that does have them, you can almost guarantee I'm booking tickets to a show. My favorite comedy club in Portland is Helium Comedy Club. They have a great atmosphere, a wonderful pre-show lounge, a fantastic cocktail and food menu, and they have the best headliners!! Some really big name comedians perform here, so if you love comedy, check out their nightly shows.

https://portland.heliumcomedy.com/

7. Street art

Portland is not lacking in this department. And this is a great way to do something that won't cost you anything! There's murals literally everywhere, you can't miss them. I really appreciate street art murals and can spend hours just walking down the lined streets admiring the art. There's also plenty of statues and other art located throughout the city and parks that you can admire if you just want a casual afternoon strolling through town.

8. Powell's Book Store

I mean, you have to! It's just one of those things... can't go to Paris without seeing the Eiffel Tower. Can't go to Portland without a stop at Powell's! If you're unfamiliar, Powell's is the world's largest bookstore for both new and used books. The place is fantastic! It takes up an entire street block in downtown Portland, and you can literally treat the store as a tourist attraction versus a regular library... no library card required! You can go in, sit down, read a book, enjoy a cup of coffee, then leave the book before you go and you never have to buy a book again! Honestly, not sure I understand the business model of this place but it definitely works for them.

9. DONNUTTTTS!!

Alright I'm helllaaa bias because everyone knows my deep love for donuts, but if you're not a fan of donuts, what are you even doing with your life? Now when it comes to these sweet treats, Portland does not lack in this area either. But how do you pick which donuts are the best? Well, everyone knows Voodoo. And if that's where you want to go, go for it! I'm not going to tell you that you should or shouldn't be a fan of Voodoo, they are a fun place! However, in my personal opinion, that's the best part about them... the fun. The atmosphere, the crazy donut designs, and everything in between. But if you want the best quality donut while in Portland... Blue Star is the way to go! This is where all the locals will tell you to go, and is easily the most popular donut chain in the state of Oregon. And let me tell you, their donuts are FIRE!! Must try the Raspberry Rosemary Buttermilk donut. Easily one of the best donuts I've had in my life!

10. Catch the Best View

I don't know about you guys, but I am a huge sucker for a view. If I go to a new city and someone tells me I have to go to such and such to see the best view of the city, you can guarantee I'll be adding that place to my list of must-dos. Just like in Bangkok, when Anson and I had to fork out $49 per cocktail each just to get the best rooftop view of the city. Luckily, the stakes aren't so high to get that view in Portland. Portland City Grill is a restaurant and bar located at the top of "The Big Pink" as the locals like to call it, which is the tallest building in the city of Portland (it's actually taller than the new city ordinance for building height but was built before those laws were in place). I love this restaurant and would recommend it regardless of the view, as their food and drink menu is actually very reasonably priced and they have a happy hour every day (I can't specifically remember the times but I think it's like 3-6??). So make sure you swing by this place to enjoy the view; catch a sunset and some cocktails.

11. Where to Stay

I can't necessarily say I'm an expert on what is the best location in Portland, however, you have a lot of great options to choose from in this city. My main recommendation would just be to stay close enough to downtown that it's easy to access everything you'll want to see and do, but that could encompass many of the surrounding districts. My first time in Portland, we stayed at a hotel right down in the city center. Which was definitely convenient for accessing nightlife and public transportation. This time, we stayed in a tiny house in the Mississippi district, which was equally as perfect for us. It was more residential, but a short walk to all of the restaurants and bars on Mississsippi, also, it was a short and cheap Uber ride to get down town. We really enjoyed the hot pink tiny house we stayed in, I'll link below if you're in to those interesting Airbnb finds like I am!