I have never loved an American city as much as I loved Portland (except New York, but I lived there, so that doesn’t count). I simply cannot explain how absolutely wonderful, lively, creative, warm, tight-knit, charming and delicious this city is. How did I take so long to discover Portland? Chances are you’re visiting Portland for a long weekend, or on a longer Oregon road trip. Either way, if you’ve got 3 days in Portland, and want to explore the best and the offbeat the city has to offer, here’s your ultimate guide to a weekend itinerary for Portland.
I managed to pack in all of this in my 3 days in Portland, with plenty of time to wander around, get lost in the streets, and even do some of these activities more than once. Please note that I didn’t do any sightseeing (minus what I got to see on the walking tour). I just wanted to enjoy the best the city has to offer – food, drinks, dessert, art, creativity, books and coffee. So nothing on this list includes the typical touristy stuff. The best things to do in Portland are simply wandering around and soaking in the essence of the city. Here goes!
10 Best Offbeat Portland Experiences for your Weekend Itinerary
1. Take a free walking tour
Free walking tours are all the rage in Europe, and my absolute favorite thing to do whenever I arrive in a new city. I’ve never seen one in an American city before, but this might be one of the BEST walking tours I’ve ever done (the other one I fell in love with was in Reykjavik). Secrets of Portlandia is run by a local, Erik, who is an excellent storyteller. You will learn more about Portland than you know about your hometown. This should be at the top of your list of things to do in Portland (tied with the Saturday Market – more below). You simply cannot leave Portland without doing this tour!
2. Explore the food cart pods
In 2008, Portland had 150 food carts. By 2018, it had 700! After the 2008 recession, locals were forced to start their own businesses and many of them resorted to food carts. Food cart pods are simply city blocks which have a large number of food carts all parked together. It’s like a food market, where you can pick between many choices. The biggest one is the Alder Street Food Cart Pod, with 35 food carts, which I returned to twice. You will find LOTS of Asian food, some Middle Eastern food, and a few interesting tid-bits. The best one I tried was the Grilled Cheese Grill – SO many delicious varieties of grilled cheese with the option of DIYs.
3. Get lost while discovering the creative and artistic boutiques of the city
One of my favorite parts of my trip to Portland was wandering around some of the artistic neighborhoods. You will struggle to find large retail chains here in Portland. Instead, everything is locally-made. In fact, a Portlander is twice as likely to have his/her own business than someone from an average American city. It is also one of the most creative and artistic cities in America, so you’re going to find some pretty rad design gifts.
Stroll around the neighborhood around the Alder Street Food Cart Pod, and check out Woonwinkel, Tender Loving Empire, Made Here PDX and Cacao. They sell offbeat Portland souvenirs, home décor, jewelry, food products, chocolates, and stationery – all locally-produced!
4. Eat lots of donuts (but not at the touristy spots)
Of course, you’ve come to Portland to eat some donuts. But please don’t waste your time going to Voodoo Donuts – the queues are absolutely ridiculous, and they have some really awful flavors. You will invariably be disappointed. Instead, hit up some of the smaller/more conventional donut shops in the city, which have freshly-baked donuts in classic flavors: Pip’s, Blue Star and Coco Donuts. With 3 days in Portland, you should definitely average one donut shop a day! Keep in mind that since the donuts are freshly made, they sell out pretty early. My first day in Portland – we got to Blue Star in the afternoon, and they had already run out! Go early, and make it your breakfast.
I can vouch for Blue Star because they also had vegan options!
5. Spend an entire morning at the Portland Saturday Market – the best you’ll ever go to!
I’m a sucker for markets. But I am always disappointed by them because they usually sell a whole lot of crap that I don’t really need. Portland Saturday Market was THE best market I’ve ever been to. It goes to show just how creative this city is. Artists are selling all kinds of USEFUL, creative and innovative products – like home décor, wooden magnets, illustrated playing cards, soaps and sprays, and so much more. Every stall was unique and made you want to buy something. We probably spent 3-4 hours here! If you want to have an offbeat Portland experience, you absolutely cannot miss this.
6. Browse books at the world’s largest independent bookstore
This is probably on your list of things of things to do in Portland. Even if you’re a non-reader like me, you won’t be able to resist Powell’s Books, which takes up an entire block of the city. They have a map of the bookstore, because there’s just no way you’ll be able to navigate otherwise. I was with a group of friends, and we decided to split up for a few hours so we could explore based on our individual reading interests, and then meet up at a designated time. No matter how hard you try, the time just won’t be enough!
Best way to optimize your time: pick a few genres you want to explore, and look at the used/discounted book racks in those sections! If you can, please buy something – it’s our responsibility to continue to keep the tradition of bookstores alive!
7. Indulge in lots of happy hours!
Portland is famous for many things, and one of them is happy hour! You will find them everywhere, and they will be PACKED. Even on weekdays. So you better make a reservation. Tear Drop was an excellent cocktail bar in Downtown, which is where you’ll be spending most of your time.
8. Eat some of the best food of your life
Portland is food heaven. It’s also coffee heaven, beer heaven, ice cream and donut heaven, brunch heaven, vegan heaven. Oh boy – it’s just heaven. I have an entire other post dedicated to the best food in Portland, so be sure to check it out.
9. Discover the best Portland has to offer: coffee and beer
Stumptown Coffee Roasters hails from Portland, so naturally, this has to be a city of excellent coffee. I stopped drinking coffee about 3 years ago now, but I usually make an exception when I travel to coffee-famous cities. More than actual coffee though, I enjoy spending quiet afternoons in local, independent coffee shops. Some options that you can check out are: Stumptown Coffee Roasters, Courier Coffee Roasters, and Heart Roasters. Some other of the best coffee shops in Portland are included here.
Portland also has an excellent beer scene, so make sure to hit up some breweries. A really fun recommendation that I unfortunately couldn’t get to was to check out Distillery Row. It’s an upcoming row of innovative Portland distilleries, making locally-distilled, handcrafted spirits. There are 12 independent distilleries, producing more than 80 unique spirits (vodka, gin, rum, whiskey and lots more) – all housed in Southeast and Northwest Portland. Every third Saturday of the month, the distilleries host a Cocktail Crawl. They each make the same cocktail, but slightly differently, so you can taste the difference as you go, and even learn how to make it! This definitely sounds like a fun way to experience offbeat Portland.
10. Rent a bike
A weekend itinerary for Portland seems incomplete without a bike ride. Portland is one of the most bike-friendly cities in the US. You can rent a bike from several places (just Google it), and spend a morning or an afternoon cycling around. You will really enjoy the many routes along the river, as this blog post lists out.
What are some of your favorite offbeat Portland experiences? What else would you include on a 3 day trip in Portland, Oregon? Let me know in the comments below 🙂