Destinations

39 Quintessential Things to Do, See, and Eat in Portland

By
Jessica Spiegel
|
Freelance Writer
view over Portland, Oregon, with Mt. Hood in background.
October 25, 2021
|
10 min read

Portland has long been the kind of city where the main “must-do” activities for visitors are whatever the locals are up to. It’s not a city with world-famous museums or monuments. Instead, it’s a place where the way of life is what draws both tourists and residents.

That doesn’t mean, however, that the list of things to do in Portland is short—this one isn’t even close to an exhaustive list. True to form, though, nothing you’ll read about below is merely a tourist attraction that locals avoid. Everything here is popular with at least some segment of Portlanders, so you’ll get your fill of people-watching as well.

Whether you’re in Portland for a short trip or scouting out a new place to hang your hat, this list of perfectly Portland things to do should keep you busy for a good long while.

Things to Do Outside in Portland

1. Hike in Forest Park

Portland has more than 200 parks inside city limits, but for many locals Forest Park is the undisputed queen. It’s one of the largest urban forests in the country at about 5,100 acres, which means it’s easy to find some solitude. It’s also instantly accessible from the city streets of Northwest Portland—you can literally walk right into the park from NW Thurman Street. There are 70 miles of trails to explore, including the popular Macleay Park and Wildwood Trails, and some are even used for horseback rides. Fun fact: The spooky, moss-covered stone ruins on the Macleay Park Trail known as “Witch House” are eminently photographable, but the building’s origins are far more pedestrian—it used to be a public restroom.

2. See Portland from the Willamette River

Willamette River in downtown Portland.

Portland is cut in two by the Willamette River, and there are several ways that can work to a visitor’s advantage. The Portland Spirit offers leisurely tours of the river, including dinner cruises, while Willamette Jet Boat Excursions turns a river tour into an adrenaline-pumping adventure. For something a little more peaceful (and DIY), check out the 187-mile Willamette Water Trail for kayaks, canoes, and SUP. If you prefer to keep your feet on solid ground, don’t miss the Waterfront Park/Eastbank Esplanade loop—it’s just under five miles of paved walkways and two walkable bridges so you can see the view from both riverbanks.

3. Act like a local in Waterfront Park

If you love a city that embraces its waterfront, thank Tom McCall. One of Oregon’s best-loved governors, he’s not only responsible for turning an ugly six-lane highway into the gorgeous stretch of riverside green space called Waterfront Park, he’s also the guy who decreed that there would be no private beaches on the Oregon Coast. The park that now bears his name is where you’ll find locals in any weather, though the park is particularly lovely when the cherry blossoms bloom in spring. This popular park is also the site of countless city festivals, including the Portland Rose Festival, Portland Pride, Waterfront Blues Fest, Fleet Week, and the Oregon Brewers Festival.

4. Explore Portland by bike

Portland loves bicycles, and cyclists love her right back. There are (often colorful) bike lanes all over the city, miles of trails connecting neighborhoods and parks throughout the metro area, a bike share program, and several annual cycling festivals and events. If you’re visiting in July, check out the Pedalpalooza Bike Festival calendar. In August, Bridge Pedal encourages everyone to enjoy a day of car-free bridges.

5. Stop and smell the roses in the International Rose Test Garden

One of Portland’s most-used nicknames is “Rose City,”  so it should surprise no one that there are some fabulous rose gardens to check out. The International Rose Test Garden in Washington Park dates from just before World War I and contains more than 600 varieties of roses today. Less famous options include the Peninsula Park Rose Garden and the comparatively diminutive Ladd Circle Park and Rose Gardens.

6. Meander through gardens great and small like the Portland Japanese Garden and Mill Ends Park

Portland Japanese Garden.

Not all of Portland’s gardens worth visiting focus on roses, though. The Crystal Springs Rhododendron Garden (free on Mondays) began as a test garden and now features more than 2,500 plants (it’s also home to a wide variety of birds). A stone’s throw from the International Rose Test Garden in Washington Park, the stunning Portland Japanese Garden covers 12 acres. On the opposite end of the size scale, the Lan Su Chinese Garden occupies a single city block downtown and was designed and built by artisans from Portland’s sister city, Suzhou. And, because it’s Portland, there’s also the quirky Mill Ends Park downtown—the smallest park in the world at a whopping two feet across.

7. Kick back in Portland’s living room, Pioneer Courthouse Square

A public brick-lined square, once a parking garage, has been affectionately known as “Portland’s Living Room” since the mid-1908s. One corner of Pioneer Courthouse Square is amphitheater-like steps, making it an ideal setting for festivals, outdoor movies, and concerts, or just the perfect place to catch some sun on your lunch break. If you need info on public transit, the TriMet office is right next to the steps. And if you’re curious about the weather forecast, look up—the Weather Machine is an art installation that changes each day at noon (with the sound of trumpets) to display a sun, a blue heron, or a dragon depending on the prediction.

8. Picnic on a volcano at Mount Tabor

The most famous volcano in the Pacific Northwest is undoubtedly Mt. St. Helens, which is about 70 miles north of Portland, but there’s a volcano inside the city limits. Mount Tabor, which more closely resembles a sizable hill than a mountain, is an extinct volcano that’s now a popular park. Paved walkways throughout the park were partly built using volcanic rock found on site. Visiting with your furry best friend? There’s an off-leash area in the park where puppers can play.

9. Commune with nature on Sauvie Island

The Oregon Coast is fantastic, but you don’t have to drive all the way to the Pacific Ocean for great beaches. Sauvie Island is about 10 miles (roughly a half-hour drive) northwest of Portland where the Willamette and Columbia Rivers meet. It’s one of the biggest river islands in the country, with ample room for visitors to spread out. There are several public beaches (including Collins, which is clothing-optional), hiking and cycling trails, and a bevy of U-pick berry farms—going berry picking on Sauvie Island is quintessential summer in Portland.

10. Savor the views at Cathedral Park

There are so many bridges in downtown Portland, it’s easy to miss out on the prettiest one in the city. The St. Johns Bridge in North Portland is probably the most Instagrammed, both for the soaring weathered copper arches on the bridge itself and the equally graceful arch supports underneath. The latter frame the views from Cathedral Park, located underneath the bridge on the eastern side of the river.

11. Look for wildlife in Powell Butte Park

As the name suggests, Powell Butte Park sits on a hill (an extinct cinder cone, to be exact, part of the same lava field as Mount Tabor) on the eastern edge of Portland. There are roughly nine miles of hiking, biking, and horseback riding trails to explore and the park is especially well-liked by bird and butterfly watchers. On a clear day, the views from the summit are spectacular.

12. Cover your transportation bases with Portland's 4T Trail

It’s not quite Planes, Trains, and Automobiles, but Portland’s 4T Trail is a fun way to see different parts of the city via public transit. The four “Ts” are train, trail, tram, and trolley—and since it’s a loop, you can start at any point. The official site recommends starting at Washington Park to take advantage of the fact that the downhill tram is free.

13. Get a glimpse of the Columbia River Gorge

Multnomah Falls.

There are dozens of excellent day trip options from a Portland home base, but few offer the quick fix (as in, head out after breakfast and you’ll be back in time for lunch) of two nearby spots in the Columbia River Gorge. Just 30 miles east of Portland is the iconic Multnomah Falls, an impressive 611-foot waterfall that’s even partially visible from Interstate 84. It’s among the top attractions in the Pacific Northwest, which means the smallish parking lot is stuffed to the gills on weekends, holidays, and anytime the weather is good. (Plan accordingly.) For a commanding view over the Columbia River, don’t miss a stop at Crown Point. Just hold onto your hat—the wind gusts coming through the gorge are no joke.

What to Eat in Portland

14. Try as many food carts as possible

food cart in Portland.

Portland is arguably the best street food city in the country, with a mind-boggling variety of food carts sprinkled generously all over the metro area. One thing that Portland’s food cart scene different is that the vast majority aren’t mobile—they’re carts, not trucks. They’re typically in groups called “pods,” often with some form of communal seating in the middle. Think the food court at the mall, only with infinitely better grub.

15. Indulge in some PNW haute cuisine

Even with so many food cart options, Portland still has a staggering number of old school brick-and-mortar restaurants, many of which have attracted attention from foodies the world over. Local chefs and cookbook authors have racked up dozens of James Beard (a Portland native, incidentally) Awards over the years, including Naomi Pomeroy (Ripe Cooperative), Gabriel Rucker (Le Pigeon), and Vitaly Paley (Paley’s Place).

16. Enjoy the early-bird special, Portland-style

Unlike the cheap well drinks and bar snacks conjured by the phrase “happy hour” in most cities, happy hour in Portland is absolutely worth the effort. You’d be hard-pressed to find a restaurant that doesn’t have some kind of happy hour menu (many even have two happy hour times, one early and one late), often with meal-sized plates at a fraction of their regular price. It's the perfect way to sample the fare at restaurants that would otherwise be beyond your budget.

17. Join the ice cream queue at spots like Salt & Straw

While Salt & Straw quickly catapulted to regional and then national fame with its adventurous and sometimes downright wacky flavors (which means there is nearly always a line out the door, even in rainy weather), it’s not the only ice cream shop in Portland worth waiting for. Ruby Jewel is a local favorite—you can even find their ice cream sandwiches in a few grocery stores. Fifty Licks, which started as a food cart, now has three locations and offers boozy ice cream cocktails as part of its regular menu. And rising star Eb & Bean takes froyo to its logical (for Portland) artisanal conclusion with a rotating menu of creative flavors, many of which are dairy-free.

18. Go beyond Voodoo for donuts

Once upon a time, a tiny, late-night, standing-room-only donut shop in Old Town filled the stomachs of revelers on their way home from the club after closing time. These days, Voodoo is more of a tourist attraction than a true local favorite. That mantle has passed to several shops in the city. Blue Star Donuts puts a gourmet twist on their brioche donuts (think Valrhona chocolate, bourbon, and creme brulee flavors). Doe Donuts is all vegan, and if you’re skeptical, their donuts will change your mind in one bite. And the beloved Pip’s Original cooks up its mini-donuts to order—try the honey and sea salt topping with a side of house-made Chai.

What to Drink in Portland

19. Celebrate hops like they’re (never) going out of style at one of Portland's many breweries

There is literally not a single month in Portland’s calendar that doesn’t contain at least one beer festival. There are major shindigs in summer (Portland International Beer Festival is in June; Portland Craft Beer Festival and Oregon Brewers Festival are in July), with smaller festivals focused on specific types of beer or brewing—including Puckerfest at Belmont Station for the sour brews, Saraveza’s IPA Fest to honor Portland’s love of all things hoppy, and SheBrew to feature the women making beer, mead, and cider.

20. Get your caffeine fix at spots like Stumptown Coffee

Stumptown coffee in Portland.

Portland’s neighbor to the north gave birth to the most famous coffee franchise on earth (and yes, there are plenty of Starbucks locations in Portland), but if you want to try something a little more local there are lots of options. Stumptown Coffee is perhaps the best known outside the region, though smaller roasters like Coava and Heart have devoted followings. If tea is more your style, head for the cafe and shop of Steven Smith Teamaker (Smith was part of the creation team behind Stash Tea and Tazo Tea, both founded in Portland).

21. Go back to school… for a pint at McMenamin's

Oregon’s very first post-Prohibition brewpub opened in 1985 and is still operating today. In fact, it’s part of what has grown into the brewpub empire of McMenamins. The McMenamin brothers have refurbished more than 60 historic buildings around Portland and the state, including a number of former elementary schools (some classrooms have become hotel rooms and gyms have transformed into movie theaters and soaking pools). 

22. Check out Portland's urban wineries

The famous Willamette Valley wine country is a great day trip, especially if you’re into Pinot Noir, but you can get a sample of local wines without leaving the city limits at the 13-wineries-and-growing list of urban wineries in Portland.

23. Sip your way along Distillery Row

Oregon has long had a reputation for excellence when it comes to wine and beer, so it was probably inevitable that it would also become a haven for distilleries, too. Pick up a passport for Distillery Row and don’t miss a stop at Westward Whiskey, a rare US-made single malt, and Freeland Spirits, one of very few women-owned and run distilleries in the country.

24. Tour a sake brewery

Winemakers talk about the importance of terroir in the flavor profiles of grapes. Sake brewers, on the other hand, talk about the quality of the water. And, according to SakéOne, Oregon has some pretty remarkable water. The tasting room is a great place to start your sake schooling, but if you can time your visit to the Forest Grove brewery to join a tour that’s even better.

Art and Culture in Portland

25. Visit Portland’s only true mansion

Pittock Mansion in Portland.

Built in 1914 by the then-publisher of The Oregonian newspaper, the Pittock Mansion sits on a hilltop (just outside the southern boundary of Forest Park) with enviable views of the Willamette River and Mount Hood. Now a house museum, it’s open to visitors and regularly hosts seasonal events, though plenty of visitors come just for the Instagrammable views.

26. Check out the Portland Art Museum

The state’s biggest art museum, the Portland Art Museum was founded in 1892 and is among the oldest art museums in the country. It has noteworthy exhibits of Northwest, Native American, and Asian art in its permanent collection, as well as sections on modern art, European art, and photography.

27. Do an art crawl or two on the first or last Thursday

Art galleries around the city have festive parties to open new shows every month. In Portland’s downtown and Pearl District, the First Thursday of the month means pleasantly crowded galleries (along with complimentary wine and finger food). And on the Last Thursday of the month, NE Alberta Street becomes the art gallery as artists set up booths to showcase (and sell) their work.

28. Seek serenity in The Grotto

The full name of the tranquil garden spaces of The Grotto is the National Sanctuary of Our Sorrowful Mother. It covers two levels, both atop and at the base of the cliff of Rocky Butte in Northeast Portland, and spans 62 acres. The lower gardens are free to visit.

Where to Shop in Portland

29. Shop (or just browse) at Powell’s Books

Powell's Books in Portland.

The biggest independent bookstore in the world, Portland’s beloved Powell's City of Books covers an entire city block downtown and the shelves are stuffed with new and used copies of just about anything you could possibly want to read. Store maps are available at every entrance. You’ll need one.

30. Pick up a souvenir (and a snack) at one of Portland's outdoor markets

Every Saturday from March through Christmas, the enormous Portland Saturday Market takes over a portion of the city’s Old Town. The market’s footprint has grown steadily since it started in 1974, with hundreds of booths showcasing local arts and crafts. If it’s picnic provisions you’re after, head to the park blocks of Portland State University each Saturday (year-round) to gather supplies at the bustling Portland Farmers Market.

31. Hunt for treasures in Sellwood

The mostly residential Sellwood neighborhood’s streets are lined with beautiful examples of classic Portland Craftsman-style homes, but for visitors, it’s the array of antique shops along Milwaukie and 13th Avenues that are often the main appeal. Start at the enormous Stars Antique Mall and try to not get lost.

Sports in Portland

32. Embrace the Spirit of ‘77

Portland is home to two professional sports, both of which have contributed to the city’s list of nicknames. The Portland Trailblazers joined the NBA in 1971, immediately acquired the moniker of “Rip City,” and won the title in 1977. You can watch the team play at the Moda Center or at any number of sports bars in the city—including the nostalgically named Spirit of ‘77.

33. Visit Soccer City, USA

Timbers soccer game in Portland.

Basketball may be more popular in the US, but Portland’s two major league soccer teams have helped to make this Soccer City, USA. The Portland Timbers, founded in 1975, joined the MLS in 2011 and won the title in 2015. When the National Women’s Soccer League was born in 2012, the Portland Thorns were one of the original teams—and they’ve won the NWSL title twice. Both teams play in Providence Park, and both enjoy record attendance. For an immersive Soccer City experience, get a general admission ticket to sit in the North End—or, more accurately, to stand and chant and cheer and clap for the entire game.

34. Cheer on the Rose City Rollers

Combine sports with something a little offbeat and you’ve got women’s flat-track roller derby. Portland’s Rose City Rollers organization has four local teams and two travel teams (one of which has won four national championships), plus leagues for kids as young as seven. RCR events at Oaks Amusement Park attract enthusiastic crowds and tickets sell out quickly. 

35. And then lace up your own skates

Once you’ve been inspired by the Rose City Rollers, it’s time to hit the rink yourself. The Oaks Park Roller Rink is open year-round (the schedule varies) and, if you’re there during the last skate session on Thursdays and Sundays, you’ll get to skate to the music of the historic Wurlitzer pipe organ.

Wonderfully Weird Things You Can Only Do in Portland

36. Find out if art imitates life

Some Portland landmarks have been famous to TV audiences since the 1980s, even though most (still) have no idea. Matt Groening, a Portland native, bestowed several characters on The Simpsons with local street names (such as Burnside, Flanders, Kearney, Lovejoy, Quimby, and Terwilliger), and fans love finding the sketch of Bart Groening drew in the sidewalk in front of his old high school. More recently, Portlandia put the city’s weirdness on center stage—you can visit some of the filming locations to see what’s fact and what’s fiction.

37. Catch a show at Darcelle’s

No landscape of Portland personalities is complete without Darcelle, the world’s oldest drag queen. Walter Cole, the man behind the sequins and show-stopping makeup, turned 90 in 2020 just before his club, Darcelle XV, became the first addition to the National Register of Historic Places for its importance in LGBTQ+ history.

38. Watch the Adult Soap Box Derby

soapbox derby car.

Portlandia told us that this is the city “where young people go to retire,” and if you can catch the Adult Soapbox Derby you might think they were right. The annual August event brings out the kid in everyone, as 40 whimsically decorated cars (and humans) steer their way down a paved path from the top of Mount Tabor. It’s all fun and games, but yes—there are actual trophies to be won. Bring a picnic, but leave dogs and strollers elsewhere.

39. Visit the coffee shop Atlas Obscura calls “casually threatening”

There are eleventy billion coffee shops in Portland, but this one deserves special mention. Rimsky-Korsakoffee House (better known as “Rimsky’s”) occupies the main floor of an old Portland house. There’s no sign outside, no website, and they only take cash. It’s only open in the evenings and serves only dessert. The lighting is terrible, the bathroom is more than a little startling to newbies, and there are a couple of tables that might make you think you’re high. Or drunk. Or both. Bottom line? You’ve just got to experience it for yourself. And don’t forget to tip the musicians.

Read more about the history and culture of Portland, and join Scott's Cheap Flights to snag amazing deals on flights to Portland and around the world.

Last Updated 
October 25, 2021
39 Quintessential Things to Do, See, and Eat in Portland
Jessica Spiegel
Freelance Writer

Jessica Spiegel is a freelance writer and editor based in Portland, Oregon. She's an obsessive knitter and loves Italy, pho, Sazeracs, the Portland Timbers, and altruism.

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