A few weeks ago, I had two days to spend in a city I’d never been to. In the weeks leading up to my trip, I had one google search consistently show up on my laptop: “What to Do in Portland, Oregon?” I had two days to explore the best, the most fun, the yummiest of Portland. After hours of research and planning the perfect itinerary, I figured I’d give you all some help. So here it is… the perfect two day itinerary to show you What to Do in Portland, Oregon.
What to Do in Portland, Oregon: Day One
I got into Portland at around 10:00 in the morning so I didn’t make morning plans for myself… I don’t want to advocate for something I haven’t personally tried, so I’m going to leave you guys to plan your own morning. Keep reading for a great plan for the rest of the day!
Lunch: Food Truck Pods
At around 11:00 I went to go get some lunch. Portland is famous for its huge food truck scene, including some food truck “pods” that can span up to four square blocks. Some of these food trucks are the standard “falafel cart” or “hot dog stand.” But some of them also get a bit more experimental! I’ll leave it up to you to decide if you’d rather shoot for new or go with comfortable, but one thing I know… with the food truck pods, you can’t go wrong.
Food Carts Portland did an incredible job of compiling every single food truck in Portland, Oregon into an easy map accessible by the internet or an app on your phone. Take a look to see just what is calling your name!
Pittock Mansion in Portland, Oregon
When looking up what to do in Portland, Oregon, I stumbled across Pittock Mansion a lot. Pittock mansion was originally owned by Henry Pittock, the founder of Portland’s newspaper Weekly Oregonian, and his wife Georgiana. Unfortunately, they were only able to live there for about 5 years before they passed away. The estate was passed down to their children and, eventually, to the Parks and Recreation department.
A visit to the Pittock Mansion allows for a transport back in time. You can see the old kitchen where the chef used to cook, see the servants’ stairwell, the beautiful staircase, and the game room in the basement.
The best part of visiting the Pittock Mansion in my opinion is everything outside of the actual mansion. The yard is gorgeous and decorated with beautiful flowers, and on a clear day you can see Mt. Hood in the distance. You can also tour The Gate Lodge, which is where the family chauffeur lived.
You can buy your tickets at the door or online before you go.
Salt and Straw in Portland, Oregon
On my way back from The Pittock Mansion, I OBVIOUSLY had to stop for some ice cream! Salt and Straw is by and far some of the best ice cream maybe ever made. The best part about my ice cream experience was that the workers at Salt and Straw encouraged as many samples as humanly possible. “There’s NO limit to samples. Here, try this one, too.” is my favorite thing in the world to hear, and I heard it a lot at Salt and Straw.
Salt and Straw is home to some pretty exotic flavors. In fact, the store allows school children to write in with flavor suggestions. This (questionable? genius?) idea is how they ended up with The Ballistic Bagel flavor, which is cream cheese flavored ice cream with bagel bits, lox, and Himalayan salt. I really enjoyed the Brie and Bleu Cheese flavor, too. After probably 8 samples, I finally I ended up with a waffle cone piled high with Carrot Cake and Olive Oil flavors.
Oh boy, olive oil flavored ice cream… so buttery and rich and creamy. It’s absolutely incredible. 1000% recommended.
Walk Around and Explore Downtown Portland
Are you wondering what to do in Portland, Oregon? The best way to answer this question is to just wander and explore. I took my ice cream and just meandered downtown. I popped into some stores to peak at what Portland could offer in terms of fashion. This is a good time to explore street art, go thrift shopping, and just get a general feel of what it means to live in Portland.
The Swifts at Chapman
If you happen to be in Portland, Oregon during September, make sure to check out the swifts at Chapman. A fair word of warning though….. If you’re scared of birds, this is not the activity for you.
Swifts are birds that have a very specific migratory patterns. They typically roost in chimneys and will often return to the same chimney year after year. In the 1980s, a flock of swifts started roosting in the chimney of Chapman school. Every day for 2-3 weeks, the swifts will swirl the chimney at dusk like a tornado and then disappear inside. More than 2,000 people gather on any given night to watch the phenomenon.
And the best part? The kids that attend Chapman School vote every year to keep the heat turned off until the swifts leave their school for the winter <3
Dinner at the Kitchen at Middleground Farms
Because I was in Portland, Oregon for a food blogger conference, I was able to attend a private event at the Kitchen at Middleground Farms. I didn’t take a cooking class there, but I do know that they do everyday events on a normal basis. Based on the dinner I ate, anything you make in a cooking class is bound to be incredible. I also have a few friends who did take the cooking class and highly recommended it!
The Kitchen at Middleground Farms is a farm on the outskirts of Portland (about 30 minutes outside the city) that does an INCREDIBLE farm to table meal. They teach delicious and informative cooking classes with themes like Late Summer Thai, Date Night Out: Rustic Italian, and Foodies Night: Taco Truck.
When I ate dinner at this beautiful farm, they made an arugula salad with fresh grilled peaches, hazelnuts, and homemade mozzarella that I almost made me cry tears of joy.
Not only would the cooking class be fun, but so is the environment. You will be surrounded by chickens, fresh gardens (which provide all of the produce for the meals), cows, and more. You won’t regret it!
What to Do in Portland, Oregon: Day Two
Breakfast at Pine State Biscuits
We started our second morning at Pine State Biscuits near our Airbnb, though we later learned that there was a location right next to the Saturday market, our next stop. Each of us ordered pretty much everything on the menu…. That was totally the right move.
My personal favorites would be the Blueberry Cornmeal Pancakes with fresh maple syrup and or the Reggie Deluxe sandwich. Runner up goes to the Biscuit Beignets. Honestly, just get it all.
Portland Saturday Market
Walk off all of that delicious food with a trip to the Portland Saturday Market. This is a huge craft show that happens every Saturday during the summer in Portland. This is a great place to get some memorable souvenirs for your family/friends back home as many of the things are homemade. We walked around the market and the surrounding park/river for a few hours, which was a beautiful way to get outside and enjoy the sunshine.
After our time at the market, we took an uber to the Japanese garden. There is a fee to enter the Japanese garden (less than $20 to enter), but in my mind, it was worth every penny. The garden is the largest Japanese garden outside of Japan. It is so peaceful and calming with beautiful coy ponds, waterfalls, miniature trees, rock gardens and more.
There is a place to sit for a cup of tea at the garden. I would recommend spending as much time here as possible. Bring a book if you want! It’s the perfect place to relax and escape.
Directly across the street from the Japanese garden is the International Rose Test Garden. If you think you’ve seen every color of rose, you are WRONG. Take the time to walk through these beautiful gardens, exploring the different colors and smells of each kind of rose. It’s endless!
Lunch at Sizzle Pie Downtown Portland
We stopped at Sizzle Pie Downtown Portland for lunch, mostly because it was directly across the street from our next stop. We each ordered the lunch special where you can get one slice of pizza and a side salad. Don’t worry, though, the slices are HUGE. And delicious 😉
Explore Powell’s Books
Okay, so I actually explored Powell’s Books twice during my time in Portland, and I didn’t even come close to seeing HALF of it. The bookstore spans an entire city block and goes up four stories, and it’s pretty much heaven. There’s an info table at the front of the store with full-blown maps so that you don’t get lost. The store is divided up into genre, and, naturally, I got lost in the cookbook section. AND the fiction section. OOPS!
I spent hours in Powell’s and didn’t even scratch the surface. I had already brought two books with me on vacation, so I challenged myself to walk out without any new purchases. Obviously, I failed… would you have expected any less?
Dinner at Departure
I had an event to go to after our visit to Powell’s, but the other gals I was with went back to relax for a few minutes before dinner. I think this is a great option after a day of so much walking and exploring.
For dinner, I’d recommend eating at Departure on the 25th floor of the Meier & Frank Building. This is a Pan-Asian restaurant where the dishes are served family style. I had so much fun going to Departure for dinner.
For starters, when you exit the elevator and walk down the hallway to the restaurant’s door, you feel like you’re walking into Space Mountain at Disney World. The hallway is decorated to look like a spaceship, with blue lights that make you feel like you’re on another planet. Once seated at the table, the restaurant has a far more normal feel. Make sure to ask for a seat by the window if possible…. The view is unbeatable!
I went with a group of 8 girls, so we ordered almost everything off of the menu (are you sensing a trend?) and each tried some of everything. Some fan favorites were the Charred Carrot Salad, the Departure Wings, and the Wok-Fired Broccoli. We also LOVED the scallops!
What to Do in Portland, Oregon Special Mention: Donut Crawl of Voodoo Donuts and Blue Star Donuts
If you get an extra hour or two, throw yourself full force into the true Portland debate…. Which is the better donut shop: Voodoo or Blue Star?
I had read online that Blue Star was the better donut choice, so this was the only place I tried donuts. Don’t get me wrong, Blue Star was good but I wasn’t mind blown. Truth be told, I wanted some crazy, over the top, sugar filled donut. This definitely was not what was offered at Blue Star (which I think most people prefer, which is why they recommended Blue Star to me).
If you have some time, try both. They’re only a mile or so from one another, so you can easily fit in a donut testing! If you do, settle the debate for me… which did you like better?
Well, there you have it folks! My perfect two days in Portland. Have you traveled to Portland before? If so, did my list of fun things match yours? Is there anything I missed? Let me know in the comments! Did you follow my advice for your trip to Portland? What did you think? Let me know that, too!
If you liked this post, make sure to check out my other Travel Guides, too!:
- Ultimate Guide to a Long Weekend in Nashville
- The Top Disney Snacks I Had in Each Park
- The 8 Best Foods in New Orleans, Louisiana
What other cities do you want me to review? Tell me in the comments below… Give me an excuse to travel, please!
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