View of Portland, Oregon with mountain in the distance.
Sunset on the Willamette River in Portland, Oregon, one of the top destinations in the American Northwest.
Sunset on the Willamette River in Portland, Oregon. Photo by

It seems as if no matter the season, the northwest is calling. If you’re in the western part of the US, Portland, Oregon is only a two or three-hour flight away. Rates for a direct round trip is affordable (Southwest and Alaska Airlines offer some of the best rates), and private lodging can be had for under $100 per night. So fly out on Thursday night and come back Sunday for a full three-day getaway.

Find your best discounted flight fare here.

Where to Stay in Portland

Consider staying at a B&B or renting an Airbnb in Portland for the weekend. Across the Willamette River, east of downtown, are some safe, affordable neighborhoods with lots of restaurants and shops worth exploring as well.

Staying out of downtown will save money on overpriced hotels and city parking costs. My girlfriend and I rented a guest house in the Brentwood-Darlington neighborhood for three nights for less than $300. We had a large modern studio space with a private patio, full kitchen, big-screen TV and couch, and a comfortable Queen-sized bed.

Find a hotel or Airbnb in Portland here:

How to Get Around in Portland

What you’ll save on lodging will pay for a rental car and some meals out. And you’ll want a rental car to drive to the coast, which I strongly suggest if you’re unsure when your next trip to Oregon will be.

We rented an SUV from AVIS, which is a short walk under the tunnel at Portland International Airport — no shuttle required — for under $150.

There was more than enough street parking where we stayed, and street parking or daily parking downtown was affordable. If you decide against the car, downtown is only 15 minutes from the airport and the train system is excellent.

Portland city skyline with Mount Hood in the distance.
Portland city skyline with Mount Hood in the distance. Photo by

What to Do, See, and Eat

Powell’s City of Books: If you love books and coffee, then this is a must. Powell’s headquarters on Burnside Street is the epicenter of west coast literary life. It is “the largest new and used bookstore in the world” — a multi-level labyrinth of new and used book rooms that could each serve as their own oversized bookstore. Centrally located in The Pearl District, this is a good location to start your exploration of the city.

Voodoo Doughnut, an independent doughnut shop based in Portland, is known for their eclectic and unusual donuts.
Voodoo Doughnut, a doughnut shop first based in Portland, known for their eclectic and unusual donuts. Photo by

Voodoo Doughnut: Adjacent to the “Portland is Weird” sign (really, it’s painted on the side of a building) is Voodoo Doughnut, the most popular donut shop in town. People line up outside of the building. But don’t worry – the line moves fast and the wait is well worth it. The shop is open 24 hours per day and makes some of the wildest donuts you’ll ever see, with both the design and the ingredients. Go grab a dozen while you’re in the neighborhood.

Tea Tasting at Smith’s: Although the weather in Portland can be temperamental, there is so much to do inside that the weather doesn’t have to interfere with your plans. Rain or pour, take a trip to Smith’s Teamaker; the original location in the northwest end of the city: it’s in an original 100-year-old blacksmith shop. The tasting room is tiny, but it’s worth a trip to this side of the city.

Considering how easily it can fill up (there are only a few tables and a few stools at the bar), head to their 13,000 square foot location on Washington Street if it’s raining to have a better chance at a table. For a reasonable $10, you get to try a flight of teas — four full cups — per person. They range from a spectrum of green teas to herbal teas. The staff is extremely passionate and knowledgeable about tea and is more than happy to answer any questions. Take home a tin of your favorite.

Steven Smith Teamaker, Tasting Room.
Steven Smith Teamaker, Tasting Room. Photo by

Shanghai Tunnels/Portland Underground: Portland, known as the “Forbidden City of the West,” has a wild history of violence, kidnapping, and drunkenness. Take a tour of The Underground and try to wrap your learn about the port town’s history, so much of which took place underneath the city streets.

Portland, like many west coast port towns, had a vast network of tunnels that expanded from building basements all the way out to the water, making it easier for merchants to move goods to and from the ships. But that wasn’t the only thing the tunnel was used for. You won’t see a ton of the underground, but you’ll see enough to make it worth your while, and learn something while you’re at it.

(Tours are currently cancelled through October 2020. Contact [email protected] with questions for future tours.)

Check out some other tour options around Portland here.

Hike Up to Pittock Mansion: There are lots of hiking options just outside of downtown; this is one of the many characteristics that make Portland unique. Just a ten minute trip from downtown, through a couple of mountain tunnels, puts you in Forest Park, a 5157-acre park, where the century-old Pittock Mansion overlooks downtown.

There are a number of hiking options to get there (and you can park directly at the mansion if hiking isn’t your thing). The trails are beginner to intermediate level, so don’t be intimidated. My girlfriend and I enjoyed a three-mile up and back hike and saw some woodpeckers. Take a tour of the mansion for $11.

The Pittock Mansion in Portland, Oregon
The Pittock Mansion in Portland, Oregon. Photo by Geoff Watkinson

Portland City Grill: Grab lunch at the Portland City Grill, one of the best views of downtown from the 30th floor on 5th It was on OpenTable’s list of 100 Most Scenic Restaurants in America for 2016, and well worth the elevator ride. It’s a great spot for a drink and a long lunch with a daytime view. The lunch menu is very reasonable, so it’s more bang for your buck; dinner entrees go up in price quite a bit. If you don’t have time to eat, but find yourself in the neighborhood, stop off for an appetizer and a drink.

Stumptown Coffee Roasters: There are droves of coffee shops in Portland, and you really can’t go wrong with any of them. My favorite was Stumptown Coffee Roasters; they’re all over the city, and they make quite the cup, with a lot of different options. If you’re unsure where to start, do a tasting at their headquarters on Salmon Street.

Aerial Tram: Most cities charge an outrageous amount for something as touristy as an aerial tram that overlooks the city. Portland, however, is not that city. For $4.70, with children under six riding for free, the short tram ride offers 360-degree views of downtown and the mountains. If you’re fortunate to get a clear day, it will be the best five bucks you spend in town. 

Aerial tram in Portland, Oregon.
Aerial tram in Portland, Oregon. Photo by Jamie Francis /

Day Trip: Cannon Beach, Oregon

A mere 90 minutes from Portland, Cannon Beach, Oregon is a must if you have the time. The beach near Haystack Rock, a 235-foot icon that sits in the Pacific just a couple of hundred feet offshore (you can walk up to it in low tide) that is part of the Oregon Islands National Wildlife Refuge, is a great place to take a walk with the family or partner.

Get a bite to eat at The Wayfarer Restaurant and Lounge, where, from your table, you can look out through the wall of windows that face the Pacific and Haystack. Even the tables in the back of the restaurant, which are set up a couple of feet above the ground floor, have a gorgeous view.

Have the braised short rib poutine — potato fries tossed with shredded braised short ribs and shallot’s Beecher’s Flagship white cheddar cheese curds with Bordelaise sauce. It’s an Oregon favorite and a hearty starter after a long, windy walk. The quaint downtown area, although touristy, is worth spending some time in. There’s an independent bookstore, lots of coffee shops, and boutique shops.

Canon Beach, Oregon.
Canon Beach, Oregon. Photo by Geoff Watkinson

There is so much else to do in greater Portland — from a half-day hike out to Multnomah Falls to brewpub excursions and wine tours, and hitting the thrift shops and antique stores. Take four photos at the photo booth at Ace Hotel (my girlfriend and I got a great personal souvenir!), or stroll through the Japanese Garden if you get good weather.

Like any city with a lot of culture, you could spend weeks in Portland without getting bored. Choose wisely, but don’t think you’ll be able to see and do everything you want to do in one weekend.

Author’s Bio: Geoff Watkinson has an MFA from Old Dominion University, where he taught writing. He has contributed to storySouth, Guernica, Switchback, The Virginian-Pilot, and The San Diego Union-Tribune, among others. Read more of his work at, or find him on Twitter: @GeoffWatkinson.

Leave a Reply

Your email address will not be published. Required fields are marked *