I just returned from a long weekend in Portland with a few friends from work. It’s the perfect escape from San Francisco. Portland is just a quick, inexpensive flight away and it has a great balance of city and nature. While it was a short trip, this Portland itinerary is anything but that. We packed a lot into our time there.
Day 1 – Friday
Arrive: Fly into Portland International Airport (PDX) in the morning. You could grab a Lyft or Uber at Island 2 outside of baggage claim on the lower level, but Portland has great public transportation, including a MAX light rail route between PDX and downtown Portland, making it easy to get around for cheap. For this trip we rented a Prius using Turo so we could drive to Multnomah Falls, Beacon Rock and Cannon Beach. If you want to go that route (which I suggest if you copy our itinerary) you can use my link for $25 off your first Turo rental.
Settle in: Check into your Airbnb. We stayed at this adorable place and loved the location. It was easy to find parking and felt central to everywhere we drove. I’d definitely recommend the rental we used, but Portland also has tons of other cool options, like this fun guest home! If its your first time using Airbnb, you can use my link for a $40 credit.
Brunch: Pine State Biscuits is amazing, so naturally it should be your first stop for fueling up before a day of exploring. They have a few locations around town. Vegetarians will be happy to know they offer a mushroom gravy!
Chase waterfalls: Multnomah Falls is a sort 30-minute drive east of Portland. If you’re lucky and make the drive on a clear day you can spot some epic views of Mt. Hood in the distance. Currently all trails on the Oregon side of the Columbia River are closed, but it’s still a beautiful drive and you can see the waterfall from a distance, you just can’t hike up close to it.
Hike: Drive a bit further east and cross the Bridge of the Gods and head for Beacon Rock. While the trail up the side of the rock looks daunting, the zig-zagging path makes it’s a fairly easy hike. Note: Washington state parks charge a $10 fee for a one day parking pass if you don’t have a discover pass.
Taste: After the hike, head downtown to taste some Voodoo Doughnuts and prepare for a sugar rush. (Pro tip: the vegan donuts at Voodoo have the softest, fluffiest dough.) If donuts are your thing, you may want to take it even further and go in search of the best donuts in Portland.
Drink: Head over to the brewery blocks in the Pearl District and try beer at 10 Barrel Brewery. Bring a deck of cards for extra fun.
Dinner: We grabbed dinner at Biwa but I wouldn’t necessarily recommend it. For better ramen, I wish we had tried Mirakutei or Kayo’s Ramen Bar.
Day 2 – Saturday
Brunch: Put your name down at Tasty n’ Sons and get excited. Their shakshuka is so good! If there’s a wait you can walk over to Ristretto Roasters for a cup of coffee or a pastry to tide you over.
Wander: The Lan Su Chinese Gardens just may be the best gem in downtown Portland. The buildings are ornate and the flowers are abundant. The gardens are great to wander, even in the rain, thanks to covered paths.
Read: Head over to Powell’s City of Books and get lost in the endless shelves, or a new story. Even if you don’t end up buying a thing, you can join the dozens of people tucked into a corner reading a book or grab a pass to peak into Powell’s rare book collection.
Drink: Back on the brewery blocks, today’s flavors are found at Rogue Brewery. Make sure to order the cheese curds and pretzels along with a few seasonal brews.
Siesta: Head back to the house and take a quick nap before dinner.
Dinner: For a simple and delicious dinner, stop by Nong’s for their chicken and rice. The peanut sauce is delicious, and they serve Thai beers alongside a popular coconut ice cream. The other Thai restaurant I really want to try is Pok Pok.
Laugh: Grab tickets to a show at Helium Comedy Club. A variety of popular stand up comedians stop through their venue and ticket prices are really reasonable. Afterwards, you can stop by the Lucky Labrador Brew Pub next door.
Day 3 – Sunday
Drive: In the early morning drive the hour and a half out west to Cannon Beach. Along the way, you won’t be able to help but stop to take in the views of fog rolling in over the pine trees.
Breakfast: Stop for a bite to eat at the Pig’n Pancake. We wanted to try breakfast at the Lazy Susan Cafe but it was closed when we arrived.
Walk: Meander along the beach towards Haystack Rock. The view is incredible. When the weather is nice, the beach is crowded, but on rainy days you may end up on the beach by yourself. Afterwards, you can always stop for lunch and a drink at Pelican Brewing. Their burgers look great.
Get zen: Back in Portland, stop by the Japanese Gardens and wander around the winding paths. In the fall the trees turn a vibrant orange, but the garden is gorgeous even after the leaves fall. If the weather is nice, you can also drive over to Pittock Mansion for a short hike and views of Portland from above.
Lunch: If you haven’t eaten already, drive over to the Alphabet district and grab lunch at Kim Jong Smokehouse. This neighborhood is really cute.
Find art: Wrap up the afternoon walking around the Alberta Arts Districts. There’s a fun mural across the street from Pine State Biscuits. You could grab a scoop of ice cream at Salt & Straw and pose for a fun snap in front of the wall. They serve funky flavors like oil oil and pear blue cheese.
Dinner: For your last night grab a family style dinner at the adorable Mediterranean restaurant, Tusk. We were obsessed with their hummus and green herbal dip. The chickpea fritters were also delicious.
Have you ever been to Portland? Let me know if I missed any of your favorite spots in this Portland itinerary!
Thanks for the tips! My friend and I are going this weekend!