Portland, Oregon is known for being quirky, artsy, open-minded and a little bit weird (okay, maybe more than a little). There’s something for everyone in this city. The downtown core is small and walkable, but there are plenty of surrounding neighborhoods that deserve some time too. The food scene is pretty incredible: think endless tucked away gems that make you want to go to three different places for each meal just so you can try as many things as possible. If you manage to get bored of the city, the Mt Hood Scenic Byway starts nearby and deserves at least a day to explore, and the Oregon coast is less than two hours away, featuring Cannon Beach and other ocean side villages.
Choose an Airbnb in one of Portland’s surrounding neighborhoods. It will give you a more authentic Portland experience and there are some really incredibly designed Airbnbs available. Below are just a handful of options:
It certainly helps to choose a neighborhood with a lot of cafes and shops nearby. We really liked the Pearl District and Boise, and we heard Alberta Arts is a good place to stay too. While it’s a nice perk to stay in a more central neighborhood, some of the best Airbnbs are a bit off the beaten path, so you might want to sacrifice convenience for a more charming place to stay. Portland is very easily accessible by car, so either way you’re never too far away from anything.
Mill Ends Park
Spanning 452 sq in, Mill Ends Park was dubbed the smallest park in the world by the Guinness Book of World Records in 1971. In 1948, the site was initially intended for a light pole — Dick Fagan planted flowers in the abandoned hole and named the tiny park after his column in the Oregon Journal.
Pioneer Courthouse Square
This public space occupies an entire city block and is also known as “Portland’s living room”. Dozens of events take place here each year, and it’s a nice place to pass through while walking around downtown.
Portland’5
Portland’s performing arts scene is defined by Portland’5, an organization that contains 5 of Portland’s most prolific theatre venues. Free public hour-long tours are offered on Saturdays every 30 min between 11:00 am and 1:00 pm, as well as on Wednesdays at 1:00 pm. The tour is really interesting and takes you through the three theatres in Antoinette Hatfield Hall, as well as the Arlene Schnitzer Concert Hall beside it (the Keller auditorium is not included in the tour as it is 8 blocks away). We highly recommend it! It made us want to go see a show, which you should definitely do if there’s something playing that interests you.
Tip: while on the tour don’t miss taking a photo of the Portland sign as you go up the stairs in Antoinette Hatfield Hall, it’s the best vantage point you can get.
Powell’s City of Books
Claiming to be the world’s largest independent bookstore, Powell’s City of Books covers 68,000 sq ft with an inventory of over 4 million new, used, and rare books. It can be overwhelming, but it’s a pretty magical place if you love books as much as I do. I could have easily spent an entire day here, but Slade and I compromised on just a couple of hours.
Pittock Mansion
Built in 1912, this historic mansion is located on hill that overlooks the entire city. After sitting empty for 4 years, the mansion was hit by the Columbus Day Storm in 1962. Portland citizens fought to save the mansion from being torn down, and it was turned into a historic house museum in 1965. Even if you don’t tour the mansion (we chose not to), it’s worth going for the view alone.
Mt Hood Scenic Byway
Starting just outside of Portland, the Mt Hood Scenic Byway is a 161 km route past mountains, waterfalls, and idyllic countryside. Mt Hood serves as the center point of it all — standing tall at 3,427 m, it is the 4th largest peak in the Cascade Mountain Range. The route follows the Columbia River east towards Hood River. There are a number of interesting sites along the way — don’t miss Vista House, Multnomah Falls, and the Bridge of the Gods. You could spend days exploring the whole area as there are a number of other waterfalls and hikes you can do.
From Hood River, you’ll head south on OR-35 towards Mt Hood. A popular ski area in winter, you can drive up to Timberline Lodge for the view of the mountain with the least amount of effort. Mt Hood is another place we’d like to spend more time exploring — it looked like a great place for skiing or snowshoeing.
After Mt Hood, Portland is only about an hour west on OR-26, past farmland and a surprising amount of vineyards and wineries. We learned that the Columbia River Gorge is a well-known wine region in Oregon.
Cannon Beach
Cannon Beach is a small coastal town just an hour and a half west of Portland. It is famous for its long beach and sea stacks, with Haystack Rock being its most recognizable landmark. The town itself is really cute with shops and restaurants dotting the streets. Don’t miss Ecola State Park, which gives you a great vantage point over the town and beach (but be careful, as many of the trails have been closed due to erosion).
Restaurants
Mother’s - Located downtown, this cute restaurant’s mission is to serve comfort food like your mother would make, and features authentic cooking from mothers around the world.
St Honoré Boulangerie - I really like this cafe chain! We had both breakfast and lunch here during our stay and the food was always great, with cute French decor to boot.
Life of Pie Pizza - Popular pizza chain with great pizza (and we like to think we are pizza connoisseurs).
24th & Meatballs - Kinda out of the way, but the meatballs were totally worth the trek.
Off the Griddle - Vegan restaurant specializing in comfort food you’d typically find in a pub (think burgers and nachos).
Drinks
The Box Social - We really enjoyed the cocktails here, plus they have a nice ambiance and decor.
Moloko - This bar is full (and I mean full) of aquariums, plus they have games and good drinks.
Dessert
Salt & Straw - Famous chain serving homemade ice cream and specializing in unusual flavors like Strawberry Honey Balsamic with Black Pepper. We opted for more typical choices (Chocolate PB&J and Gingerbread Cookie Dough for me, classic vanilla milkshake for Slade) and both were delicious.
Blue Star Donuts - Forget Voodoo Donuts! Blue Star Donuts had more appealing options and the donuts were awesome. No line out the door either!
Coffee
Coava Coffee Roasters - Well-known chain serving delicious coffee and good pastries.
Tov - Egyptian style coffee in a double decker bus. It doesn’t get more Portland than this.
We really enjoyed how different Portland is. There’s lots to see and do both in the city and nearby areas, so we hope this post helped you narrow down your list! Do you have questions for us, or other Portland suggestions? Let us know in the comments below.
Happy travels,
Maria