In late August, The New York Times published an updated version of an article they had initially written 10 years ago — an itinerary of activities to accomplish in 36 hours in Portland. As a lifelong resident of the Portland metropolitan area, I found this article quite inaccurate. Though there may be elements to Portland that are culturally different from many major American cities, it is much more than what meets the eye.
To get more information about Portlanders and how they spend their time, I spoke to Calypso Kupper ’29, who was raised in inner Southeast Portland and the Foster-Powell neighborhood. Kupper gave valuable insight on how Oregonians, especially young adults, enjoy the city. She described Portland as a city with a very distinct character, but did not portray weirdness as its defining characteristic. When asked about some of her favorite cheap things to do in Portland, Kupper gave some great advice. With her recommendations in mind, let us see what a local’s guide to 36 hours in Portland would look like.
Friday
Hopefully, your walk around the Portland International Airport after your arrival has provided you with a glimpse of the cuisine and culture this city has to offer. Having been recently renovated, PDX has earned itself a spot on the The World’s Most Beautiful Airports List for 2025, and boasts storefronts for multiple local restaurants and businesses, as well as a main terminal with a slatted roof built using local wood.
Once you have gotten out of the terminal, take a look around PiPH by Paper Epiphanies, a feminist card and stationery store that will ease you into the Portland vibe. At this point you are likely hungry, so take the MAX light-rail, a bus or an Uber to one of the many food cart pods around the city. Cart Blocks is a great pod located in the heart of the city, featuring many family and immigrant-owned restaurants. One of the pod’s most interesting establishments is Rachel and Rose, a converted London double-decker bus that serves drinks with rooftop seating.
To finish off the day, enjoy some local art. Travel Oregon’s performing arts calendar provides a list of various plays, movie screenings and live music in Portland. If you are on a tight budget, not to worry — student discounts are available.
“Thanks to arts for all, if you’re a student, a senior citizen or receiving any sort of government assistance you can get $5 tickets to a lot of local productions,” mentioned Kupper.
If you are still hungry, Burnside Street is littered with a wide variety of restaurants and food carts where you can enjoy a bite. Go get some rest in your hotel — hopefully a McMenamins institution — since you have a busy day tomorrow!
Saturday
A classic Portland weekend will often begin with a trip to the Saturday Market or a light hike in one of our many parks. The Saturday Market is open every Saturday from March to December and is a great place to experience local food and culture.
If that is not your jam, Kupper mentioned that a walk around the Columbia River Gorge is a beautiful way to get out in nature. Investing in a local field guide at Powell’s Books can be a great way to make the most of your hike, and you can make a game of identifying local species of flora and fauna. If you do not fancy fighting tourists for a photo in front of the iconic Multnomah waterfall, Kepper mentioned a few other interesting locations to hike.
“For cheap fun, we’ve got a bunch of free hiking spots: Forest Park, Powell Butte, Rocky Butte, Mt. Tabor and more,” said Kupper.
Around brunchtime, a good meal is probably appropriate. Screen Door, a southern restaurant with two locations in Portland and one inside the Portland airport, is a definite favorite because of their chicken and waffles. Bernstein’s Bagels is also a spot that many Portland residents love and offers a wonderful pumpernickel bagel that is only available on weekends. If you are looking for something in strict lunch territory, PDX Sliders offers incredible sandwiches with a variety of fillings, all inspired by Portland’s bridges and districts.
It is a day for cultural exploration, so a trip to one of Portland’s many local libraries or independent movie theaters is due. The Multnomah County Central Library is beautiful and a great community space where you can explore the shelves and cozy up with a nice book free of charge. If you are looking for some cheap concessions and to support an independent business, Studio One, McMenamin’s Kennedy School theater and Cinema 21 are all fantastic local independent theaters. If you are in the mood to learn, the Oregon Historical Society offers free tickets for Multnomah County residents — your LC ID can be used as proof.
As the night is winding down, why not enjoy a walk along one of Portland’s 12 historic bridges. The Burnside Bridge and Tilikum Crossing both provide beautiful views of the Willamette River. Tilikum Crossing is one of Portland’s newest bridges and takes you from the Oregon Museum of Science and Industry to Oregon Health and Science University. The Hawthorne Bridge is simply a personal favorite of mine, and having driven on it every day to make my high school commute, I know the East Side has wonderful businesses and is incredibly beautiful.
If you are looking for a sweet treat to end your day, Salt & Straw is an obvious choice. However, I have personally always preferred a more understated spot: Cheese and Crack Snack Shop. They offer soft serve and a variety of house special sundaes, as well as cheese and cracker platters. Fifty Licks and Dairy Hill are also incredible options for a frozen dessert.
Sunday
During your last morning in town, I would highly recommend supporting one of our many local cafes. Kupper recommends The Worker’s Tap and Cafe, a collectively owned bar and breakfast spot that hosts a wonderful community hub.
After a lovely snack, it is time for one last nature stop before you leave Portland. Take Interstate 84 out to the Columbia River Gorge, one of Kupper’s favorite natural spots in Oregon. It is a bit past the airport, but you truly will not regret seeing it. On your way out, try stopping by Cascade Locks, a small town in Hood River county featuring Brigham Fish Market, an amazing Indigenous-owned seafood restaurant, and the Eastwind Drive-In, a great local ice cream and burger stand.
Now that you have experienced a taste of what the great city of Portland has to offer it is unfortunately time to leave. Enjoy every step through PDX on your way out, and we hope to see you again soon.
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