Fill a Weekend in Portland OR

Portland is a nice-sized city, perfect for a weekend getaway. I have been to Portland just four times, but I feel good about recommending things to do, where to eat, and places to stay. Simply put, every time I go to Portland I have an incredible time… so if you follow my lead, you will too. Read on to find ways to spend your weekend in Portland.

What to See

Powell’s City of Books deserves a post all it’s own, which I am planning for next week. Imagine your favorite used book store, plus your favorite new book store, and then multiply that by about 7. Now you’re getting the picture of this legendary destination.

Providence Park, the Portland Timbers Stadium is currently undergoing an expansion so I only got to see it from the outside. The team is known for its rabid fans so attending a game is sure to be a thrilling experience. If you want to book a stadium tour you must contact them in advance since they don’t operate public tours regularly the way other teams do. Once the expansion opens, I could envision a regularly scheduled tour in the future.

The Saturday Market is one of my fondest early memories of Portland. It is also one of their most famous family-friendly draws. You can peruse handmade goods and other small business vendors, and taste food from around the world. I vividly remember my first time in Portland- I was only there for a day and my friend and I checked out the Saturday market and a few record stores downtown. I can still picture myself sitting on a grassy area adjacent to the river and trying falafel for the first time.

Where to Eat

Brunch

If you’ve watched Portlandia, you might remember an intense episode about brunch. I haven’t had to wait in a line wrapped around the block, but then again I err on the breakfast side and get food in my belly around 9am. I recommend Hesler’s on Alberta (pictured, my smiling mug above) in the Alberta Arts District if you happen to be outside the downtown area. Otherwise, ask your hotel’s front desk or airbnb host for their favorite brunch in walking distance.

Donuts

Mention you’re headed to Portland, and 9 out of 10 people will tell you about the time they had a Voodoo donut. If you want creative donuts with out-of-the-box toppings (I had Captain Crunch) then get ready to wait in line for Voodoo. I think it’s worth making time for once, but not each time you go to Portland. For a less edgy but more delicious donut, visit Blue Star.

Ice Cream

I’m going out on a limb and saying that Portland was one of the first cities to embrace “weird” flavored ice cream. Doug had a scoop of marionberry-habanero-goat cheese, for example. Salt & Straw is Portland’s most famous ice cream establishment which has made its way south: there are now outposts in LA and San Diego! Another area ice cream shop is Ruby Jewel.

Lunch/Dinner

As I mentioned, excellent food and drink abounds—look for a busy place and you know it will be good. There are two standout family-friendly restaurants I want to highlight, though.

Elephants Delicatessen is the first one; it was recommended to me word-of-mouth so I had to check it out. I can be indecisive when it comes to food, but this restaurant caters to that. You can order a little bit of everything and then tally it all up at the checkout counter once you’ve filled your tray.

The second restaurant(s) I want to highlight is McMenamins. What a concept—the restaurant owner owns dozens of locations and each is customized to the history and style of its building. Love this idea!

Find another weekend destination here.

Where to Drink

Coffee

Here’s a cool thing about Portland: Coffee will be outstanding pretty much everywhere. Even a nondescript coffee cart has to up its game to survive in a city like this one. Stumptown is the obvious famous choice (they have a huge outpost in the airport). Dutch Bros is more of a sweet treat than a straight coffee, which honestly has its place and time. If you want to get serious about your craft coffee, check out this Eater map of 20 Portland coffee shops.

Beer

Portland is one of America’s great beer cities (see: San Diego, Denver, Chicago). Make an afternoon stop in a tasting room, I’ve visited Deschutes, Rogue, Widmer, Burnside, and Hair of the Dog. Hint: If you want amazing food along with your drink, Deschutes downtown is where you want to be. For a local’s take, Eater comes through once again with a list of popular breweries.

Happy Hour

Happy Hour in Portland is a way of life. The scene is very competitive and you can benefit from great prices and check out a variety of places before 7pm. (Here’s a HH guide form a year ago that may come in handy).

Where to Stay

Most recently, we stayed riverfront at Hotel Rose, a Staypineapple hotel. I enjoyed it and you can view my full review here. The hotel was less than a block from the MAX station so getting to and from the airport was cheap, if a little slow.

Previously, we stayed in an airbnb located in a more residential area, the Alberta Arts District, and I loved getting to feel like a local. Before that, we stayed at the Ace Hotel Portland, a forever favorite—I love their ambiance.

Overall, if you want to explore a new city and don’t have a ton of time, Portland is an excellent option. It is pretty small in area and jam-packed with cool places to explore.

Thanks for stopping by! Looking for a new city to explore? Find a few more city itineraries here!

All photos by Doug and Staci Jackson for The Voyageer.