An Insider’s Guide to Portland, Oregon (10 Must-Do Activities)

Portland, Oregon is one of America’s most mercurial cities– at once hipster, anachronistic, and culturally self-serious, but also fun-loving, beautifully entwined with nature, and rife with charming Americana. 

In addition to excellent coffee, donuts, and bookstores, the city is famous for its quintessentially normcore fashion, wild- and foraged locavore food scene, offbeat cultural happenings, and a pronounced sustainability ethos that runs through all aspects of commerce in the city, from vintage clothing shops to secondhand bookstores to naturopathic healers and every seed-to-table restaurant and activist art display in between. 

Portland’s beautiful, historic houses and the Willamette River that snakes north through the city create a backdrop of breezy ease that pervades this unique region of the Pacific Northwest. Portland, moreover, is a city that feels like a small town– and nowhere is that more apparent than in the local slang, which pervades many subtle aspects of navigating neighborhoods in and around Portland.  

Some local slang to know: First, “Multnomah” (pronounced “mult-NO-mah”, the name of the county that comprises most of Portland– it comes from the native Nematlnomacqu, the name of the tribe indigenous to Sauvie Island). 

Also, “NoPo” (short for North Portland), which is known for its laid-back hippy vibe as well as plenty of great restaurants and local coffee shops. 

Finally, “Trendy-Third” and “Trendy-First”, aka NW 23rd and 21st Avenues, are the locations of many of the trendy shops and boutique restaurants that appeal to the well-heeled. Pearl District, on the other hand, is the place to go if you want to gallery hop. (Just some verbiage to consider if you want to be in on the local vernacular!)  

Portland, meanwhile, is also called “Rose City” because of the gorgeous Portland International Rose Test Garden (more on that, below) and also the fact that roses bloom across community gardens and front lawns all over the city. 

^ It’s a charming, nuanced aspect of these rainy climes that the most beautiful and also the most fragile flowers– roses– thrive in this generally overcast climate. Take some time to notice them. 

Accordingly, the best time of year to go to Portland, Oregon is in the late Spring and early Summer, when the sun is more likely to be shinning and morel season is at its peak. During this time, of course, you must get coffee at a local shop and spend some time outside (either biking, foraging, shopping at farmers’ markets, or just exploring the neighborhoods), as all of those things are better when it isn’t raining or cold outside.

And when it is raining, well, you have bookstores, microbreweries, art galleries, thrift shops, and vintage boutiques for that. 🙂 

Naturally, you’ll also need to watch at least one episode of Portlandia before you go. All of the inside jokes will make more sense once you get here. 

Below, scroll our guide to the best things to do in Portland, Oregon. Read this article top to bottom to get an overview of the cool things that this city has to offer, then go back and screenshot what you want to check out. Better yet, Bookmark this guide for easy reference on your trip! We update it regularly.  

Welcome to PDX and enjoy!  

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Coffee.

You have to get good coffee in Portland; Portland is one of the best cities in America for coffee! The best way I can describe the culture here is this: coffee is to Portland what bagels are to New York. It’s a quintessential food item synonymous with the place that serves as an unofficial mascot of local culture.  

Accordingly, there’s no shortage of good cafes in Portland. But, some of the best coffee in Portland is apt to be found at Good Coffee, Cathedral Coffee Shop, Albina Press, Proud Mary Cafe, Coava Coffee Roasters, Fuller’s Coffee Shop, and the iconic Portland original: Stumptown Coffee Roasters. (<— If you can only go to one place, I’d go here or to one of Good Coffee’s several Portland locations.)   

All of them are great, and every local has their preference. But if you check out any of the stops in this guide, you’re bound to get “the essence” of what Portland coffee is all about.  

Spoiler alert: coffee in Portland is something of a religion, and as such it’s a bit more “sour” than casual coffee drinkers may be familiar with. The overtly “roasted” flavor of the beans at many mainstream coffee establishments– like, say, Starbucks– is actually the result of over-roasting the beans.

Thus, delicately roasted coffee has a different, punchier taste. Coffee snobs tend to get behind Portland coffee, but those who are merely casually coffee curious might not prefer it. 

Either way, if you never have coffee in Portland, you’re doing it wrong! 🙂  

Doughnuts.

Perhaps because of Portland’s robust coffee culture, doughnut culture is equally strong here. Doughnuts, moreover, are “a thing” in Portland. 

Whether you call them “doughnuts” or “donuts”, VooDoo Doughnuts in Old Town Portland is sort of like a Times Square destination in the city. It’s very kitschy and the doughnuts aren’t even necessarily that good (IMHO), and yet it’s an iconic spot most people feel compelled to visit just for the experience. (This place is very eccentric.) 

You’ll know you’re nearby when you see the line and people nursing the iconic pink boxes. But truthfully, there are better doughnuts elsewhere in Portland.

• Insider Tips

Some of the Best doughnuts in Portland, in my opinion, can be found at Blue Star Donuts, which has locations in North Portland, Southeast Portland, and South Waterfront. They once had a seasonal Maple Bacon Donut that was as life-affirming as it was unexpected. (They’re known for their boutique foodie flavors, and all of them are so delicious!)  

I also like Fills Donuts— they make unique “Berliner”-style donuts in seasonal flavors like chocolate peanut butter and masala chai, as well as traditional German crullers. They even offer rare “savory” donuts, like the pimento-stuffed cheese donut. (<— You have to try it to understand the magic.) 

Finally, Doe Donuts sells vegan donuts and ice cream in a variety of classic and artisanal flavors. Take, for example, the Tahini Pistachio glazed donut and the Pineapple Coconut Fritters, which are amazingly rich. I also love the clever Portland Fog Donut, which is flavored with Earl Grey tea.

^ Ultimately, however, the filled Tiramisu donut and incredible Cookie Butter Twists are the real must-tries for first-timers. Trust me. Seasonally-inspired vegan donuts are about as “Portland” as it gets. 

Books.

No trip to Portland would be complete without a stop at Powell’s Books on Burnside Street. Powell’s Books is the World’s Largest Independent Bookstore, which sells new, used, rare, and out-of-print books. (It only makes sense that this would be in Portland!) 

For the quintessential experience, I recommend going to the local author’s section in the downtown location and buying a local book (either locally-themed or by a local author) like Chuck Palahniuk’s Fight Club or Cheryl Strayed’s Wild. They also have great foraging, outdoor adventure, music, fiction, and science fiction sections.

Ultimately, however, this multi-level bookstore really does have it all. (Including a cute cafe and some locally-made, non-book gift items, as well.)  

Be sure to wander and check out the rare book room (some people say it’s haunted, but that’s another story entirely). Here, you can find rare books like a 1st edition of The Lord of the Rings on sale for $5,000. 

The first time I spent meaningful time at Powell’s, I also spent hours leafing through works by local authors, looking at the gluten-free cookbook section, and I also bought a picture book of Ansel Adam’s old photographs of National Parks. This anecdote is very telling and reflective of the area’s culture. If you’re a book-lover headed to Portland, be sure to add a stop at Powell’s to your itinerary! 

• Other cool Portland bookstores of note

Other great local bookstores in Portland include Annie Bloom’s Books (which has an in-store cat); Broadway Books; and Mother Foucault’s Bookshop, which is a great (if incredibly hipster) place to shop for secondhand philosophy, poetry, non-fiction, and foreign-language titles. 

And in a pinch, Monograph Bookwerks (for used books) and Ampersand Books (for indie books) are also great!  

^ Of these additional independent book retailers, I like Broadway Books the best, as it is super welcoming, female-owned, and has a great travel section. (<— And, like Elliott Bay Book Company in nearby Seattle, it’s rife with local charm!)

They also host cool author events that have featured, in the past, public figures and writers like Cheryl Strayed, Carrie Brownstein, and Floyd Skloot.  

Hiking + Outdoor Adventure.

One of the most famous outdoor landmarks in the greater Portland area is a waterfall viewing spot from a bridge at Multnomah Falls.

Here, you can take in iconic views of the tumbling water from a quaint little arch bridge that passes right in front of it. (Talk about white noise…) It’s beautiful any time of year– even in the winter! (^ That’s a picture of it, above.) 

Hiking at Wahclella Falls Trail at the Columbia River Gorge, 30 miles east of Portland, is also lovely if you have a car. The geography of this region is unlike anything else in the country– a visual mix of South-Western canyon style topography and lush, almost Pacific-Island-like grandeur when summer hits. 

Sauvie Island, meanwhile, is 15 minutes North of downtown Portland and sits at the confluence of the Willamette and Columbia Rivers. It’s known for hiking, water activities, and exotic things like horseback riding, but this river island the size of Manhattan is also a go-to spot for berry and pumpkin picking. It’s a great place to get out in nature not too far from the city!  

(There are also a number of amazing outdoor adventure outfitters in Portland, which you can read more about under “Cool Shopping”, below. If you’re looking to buy outdoor gear, either new or secondhand, Portland is an awesome place to do it.) 

Morels.

When it’s morel season in Portland (generally from March-May) you’ll know it. Seemingly every restaurant in the area will feature this locally-foraged mushroom on their menus until the season passes. You’re also apt to see morels take over the local farmers’ markets, like the Saturday Farmers Market at Portland State University. (<— Worth checking out!)  

Foraging, moreover, is a huge culture in the Pacific Northwest. This is why this region attracts foragers from all over the country. Naturally, however, locals are fiercely protective over their favorite spots, so don’t expect any of them to share any secrets of the trade. 

Still, if you know what you’re doing, Portland is a great place to wander into mossy forests and see what you can find. The abundance of rain and mild annual temps ensure that there’s always something unique and intriguing growing, whether it’s mushrooms, berries, exotic mosses, or tasty leaves just waiting to be plucked. 

Nature parks and preserves that are ideal for foraging in Portland include Forest Park, Powell Butte Natural Park, Tryon Creek State Natural Area, Marquam Nature Park, and Lewis and Clark State Park. These make excellent foraging destinations because these areas aren’t sprayed, so you’ll know everything you get is clean and untarnished by any pesticide or herbicides. 

For more info on how to forage morels, go here.  

Quirk.

• Movie Madness is a Portland Institution. Here you can see Julie Andrew’s iconic dirndl from The Sound of Music, Mike Myer’s lime-green suit from Austin Powers, the knife from Psycho, and other famous Hollywood movie paraphernalia.
• Other Unofficial But Quintessentially “Portland” Things: brothels, ghosts, “shanghaiing” in the underground tunnels below the city (look it up), and, um, drag queens. 
• Portland is America’s strip club capital. No, seriously: going to strip clubs is a huge thing here. Many locals do it socially, even over dinner. We’re not saying you should go to, say, Golden Dragon Exotic Club, the Kit Kat Club, or Mary’s Club– but those might be fun places to experience this unique, erm, culture.  
• Chem Trails? Yikes. Be careful who you start conversations with at Portland bars. People in this part of the country are prone to believing conspiracy theories, which– depending on your persuasion– is either interesting or terrifying. Just something to keep in mind! 
• The Heathman Hotel is a 3-minute walk from the Portland Arm Museum and lots of famous authors and celebs stay here, as well (from Sting to Charles Barkley). David Sedaris loves it. There are paintings by Andy Warhol, antique fireplaces, plenty of interior plants and foliage, a chandelier from the American Embassy in Czechoslovakia, etc. People say it’s haunted, but for a certain crowd, that’s part of the charm. If you’re looking for a quirky hotel to stay at in Portland, this one’s your best bet. 

Brunch.

Like New York City, brunch in Portland is sort of religion. Unlike New York City, however, Portland isn’t so self-serious about it.

Perhaps it’s because of the ease of getting wild salmon, fresh morels, and forest herbs, but the omelets and hash in this part of the country are fabulous. (As is every breakfast dish that features local, Pacific Northwest salmon.) 

Pine State Biscuits is known for its epic Southern-style biscuits and biscuit sandwiches, like the Reggie Deluxe (above shown). They also do lovely foodie-flavored homemade pop tarts, like this pretty Lemon Ricotta & Rhubarb showstopper. 

Sweedeedee offers artsy, thoughtful, locally-sourced diner-style breakfast and lunch, with menu items like savory brown rice porridge (with soft-boiled egg, sleeping beauty cheese, and chili oil) as well as heart eggs and rustic toast dishes. It usually has a line, and with good reason.   

Locals also love Le Happy Creperie, and Olympia Provisions has the best dang breakfast sandwiches around.  

Other wonderful breakfast restaurants in Portland include Milk Glass Market (which has a wonderful selection of seasonal pantry items sourced from local farms); Vivienne (kitchen pantry + culinary books!); Spielman Bagels (best bagels this side of New York!); Loretta Jean’s (a pie bakery with fabulous pastries and biscuits); and Maurice (upscale Nordic-French fare, ideal for nicer sit-down brunch). All so good!  

Coastal Drives.

The coast of Northern California as it segways into Oregon is some of the most beautiful coastal driving in the country. (I say this as someone who used to live in Hawaii and summers in Maine.)

Take the Historic Columbia River Scenic Highway up the coast for some of the Pacific Northwest’s most picturesque views. Or, drive the Pacific Coast Scenic Byway— a classic American road trip– for incredible sunsets on Gold Beach.

^ Both are beautiful and showcase plenty of compelling scenery, from summer sunflower fields to snowy Mt. Hood to views of the Columbia River Gorge.

Volcanic Legacy Scenic Byway is also a lovely drive around Klamath Falls in Southern Oregon. 

For more information on these and other scenic coastal Oregon drives, go here. If you venture outside the city in the summer or fall, you’re bound to discover several quiet, beautiful stretches that feel like private escapes. Coastal Oregon, in my opinion, is one of the most ruggedly beautiful and underrated parts of the country.  

Music, Art, + Film. 

Record-lovers, indie music junkies, and cinephiles love Portland, and with good reason. Mississippi Records and Little Axe Records are great Portland record shops worth exploring. (<— Think of them as Portland’s answer to SF and LA’s Amoeba Music.) 

Portland Art Museum, meanwhile, has cool regional things like comprehensive exhibits on the work of iconic wilderness photographer Ansel Adams, light artist Dan Flavin, and Japanese ceramist Katsumata Chieko, as well as curated retrospectives like Frida Kahlo, Diego Rivera, and Mexican Modernism. They also have a cool gift shop (a great place to buy aesthetically pleasing souvenirs!). 

Additionally, Nationale, Yale Union, the Adams & Ollman Gallery, and Lumber Room are also great, minimalist venues in which to explore the local art scene. 

(Plus, the iconic KEXP radio station, which broadcasts from nearby Seattle, is within range for great driving music.)  

• Cinephiles Love These Theatres

Film lovers, meanwhile, should check out Hollywood Theatre (a modern-historic movie house favoring indie flicks) as well as Cinema 21 (also historic). 

Laurelhurst Theater is an Art Deco theatre showing first- and second-run films along with food and drink service. 5th Avenue Cinema is a very Wes Anderson establishment, and the NW Film Center offers classes and hosts festivals.

Bagdad Theatre is another archival venue where One Flew Over The Cuckoos Nest premiered in 1975, initiating what has remained since a stalwart community of alternative and indie film lovers in Portland.

Finally, The Church of Film coordinates gatherings for obscure film lovers (a very Portland thing to do!), and McMenamin’s Kennedy School Theatre is just a charming place to watch a flick.  

Movie Madness (as previously detailed above) also has video rentals, in addition to the kooky costume collection. 

Portland International Rose Test Garden. (+ Other Beautiful Gardens!)

Portland International Rose Test Garden is absolutely gorgeous in the blooming season (spring and fall). In my humble opinion, it’s even cooler than The Rose Garden at the New York Botanical Garden– if only because of its rugged location and organic, lush layout. This is my favorite garden in Portland, as it’s also the most unabashedly delightful. 

Located on a high crest within Washington Park, the garden’s colorful flowers delight the senses with their beautiful hues. Plus, the garden itself overlooks the city in the distance, making for a really charming photo op. (Sort of like Queen Elizabeth Park in nearby Vancouver.) 

The garden boasts over 650 varieties and 10,000 rose bushes, in addition to 2,500 rhododendrons and azaleas. (<— These can bloom as early as late February.) Peak rose blooms in Portland take place between April and October, which, again, is why summer is an ideal time to visit. 

For the best experience of peak blooms, visit the Portland Rose Garden in June. Portland is called “Rose City”, after all. Don’t miss out!    

• Other Beautiful Portland Gardens + Nature Sites Worth Exploring

Forest Park (5,200 acres) is the largest city park in America, and it has plenty of nice trails and birdwatching.

Lan Su Chinese Garden has amazing pagodas, lots of lunar New Year programming, and a quaint tea shop.

The Garden at Elk Rock is a lovely 13-acre garden and estate overlooking the Willamette River from a hilltop perch in Dunthorpe, Oregon. 

Portland Japanese Garden is a serene, camellia-filled 5.5-acre mountaintop plot full of zen-like waterfalls and manicured Japanese-style gardens.  

Laurelhurst Park and Irving Park also offer green respites around the city (and you’re apt to see plenty of slackliners, FWIW).

Hoyt Arboretum, meanwhile, is a gorgeous living tree museum that’s free to explore. Trees in this part of the country are particularly majestic! 

Pizza. (at No Saint or Lovely’s Fifty Fifty)

Pizza might initially feel like an East Coast thing, but the rich breadmaking culture of the West Coast undergirds a beautiful sense of reinvention happening around pizza in Portland right now.

No Saint and Lovely’s Fifty Fifty both do an excellent job of showcasing what makes so-called “West Coast pizza” so unique and compelling. (E.g., Seasonal and foraged ingredients atop hearty sourdough-inspired crusts usually served without tomato-based sauces, to let the other topping flavors shine through.)

Ultimately, if you can only try pizza here once, opt for Lovely’s Fifty Fifty. This charming new-age institution is helmed by chef-farmer Sarah Minnick, who uses super-seasonal ingredients like sunchoke and watercress to top her generously intentional pies. She also bakes her dough from a robust sourdough recipe that yields an extra sour, branny crust; a unique experience even within the changing landscape of pizza culture these days.

^ If you love to eat truly local, one-of-a-kind foods, try Lovely’s farmers market-inspired pies for the quintessential Portland pizza experience. Just be sure to arrive early– even in the Portland drizzle, there will be a line. 

Cool Shopping.

I once bought a plaid shirt that’s missing a button at Next Adventure in Portland, and it’s somehow become the best thing I own. I love it! It’s an amazing place to stop before hiking or camping as they have gently-used tents, sleeping bags, and other gear that could easily fetch hundreds of dollars new.

^ Outdoor adventurers: stopping here is a must! Plus, it’s like recycling! The whole concept is very, very Portland. I also once got an amazing vintage Mountain Hardware jacket here, which was so much cheaper than new it almost felt like robbery.  

Kat + Maouche, meanwhile, features vintage Moroccan rugs, traditional art, and modern design in their beautifully-curated shop on NW 4th Ave. The whole aesthetic of their store gallery is amazing; it’s very Brooklyn-by-way-of-Paris meets the laid-back earthiness of the Pacific Northwest. The curation, moreover, is on point. 

The Red, White, and Blue Thrift Store is a no-frills paradise for used clothing and junk-lovers. Locals love it! It’s wild. 

Rachel Sees Snail Shoes offers classes and kits for learning how to make your own sandals (literally! so Portland!) and there are also occasionally great sample sales on her super trendy, artsy, one-of-a-kind shoes.

^ Be sure to check her website for the latest info on classes, as the owner recently took a sabbatical in Los Angeles, and as of this writing, she’s still there. DIY folks and artists love this.   

Frances May, meanwhile, is a super Portland-y clothing boutique that wouldn’t feel out of place in Brooklyn or Los Angeles, either. Shop Boswell has a focus on sustainable clothing and craft sartorial brands.   

7sisters is another champion of the slow fashion movement, with great apothecary items. 

Oko has gorgeous vintage and antique jewelry, and Una has beautifully-curated clothing, jewelry, and housewares from international designers. Stand Up Comedy, meanwhile, sells clothing from extremely avant-garde designers. Zig Zag Wanderer is also good for vintage and thrifting.  

Olo is Portland’s signature hipster perfumer of sorts, specializing in roll-on fragrances. 

Midnight Sunlight is good for vintage lighting, furniture, and objects.

Cargo has a little bit of everything, specializing in “curious objects” from the realms of clothing and furniture to apothecary, art, jewelry, textiles, and decor sourced from artisans and hand-makers around the world. It’s a whole scene— you could easily spend hours here!  

Finally, Solabee Floral & Plants is a must-stop for plant lovers and botanical folx. In addition to being a full-service floral studio, they are experts at turning any space into a personal jungle. Whether you’re visiting Portland and want to collect a new plant as a souvenir or you live here and are interested in appointing your space with greenery, it’s an enchanting little oasis.  

Notable Annual Portland Events

• Every May, thousands of visitors flock to the famous UFO Festival in McMinnville, OR, for four days of parades, panels, costume contests, and expert speakers. 
• The OMSI Planetarium hosts star parties for armchair astrologists and more. 
• The epic corn maize and Pumpkin Patch on Sauvie Island is open annually each Fall. It’s great for kids and adults, alike. Check their website for the latest hours and info. 
• The PSU Farmers Market takes place every Saturday, year-round. The King and Lents International Sunday Markets begin in May and June, respectively. Find more info on Portland’s Farmers Markets here. 

Other Helpful + Cool Things To Consider

• Wanna stay in a cool, trendy Portland hotel? Hotel Grand Stark and The Hoxton Hotel are great options. AirBnb is also available in Portland, and can often lead to very authentic experiences of the city that are offbeat in a good way.  
• Beekeeping and Guerilla Gardens abound in residential areas in and around Portland. 
• People here love to bike! Renting your own set of wheels is a great way to explore the city. Everybody’s Bike Rentals is a great place to rent from; they also offer unique bike tours of PDX. 
• Dairy lovers should definitely swing by Tillamook Creamery’s Market at the Portland Airport. If you can’t make the 1 hour, 20-minute drive out to Tillamook, Oregon to try the iconic ice cream at the factory, this is the next best thing!  
• Cathedral Park can be very charming and worth a visit. The arches below Saint John’s Bridge bi-sect the park and create a cathedral-like effect above the expansive lawns. (Ideal for sport, play, lounging, and picnics.)    
• Bob’s Red Mill Flour is located in Portland. Iconic brand’s owner is obsessed with the history of milling, and has all kinds of cool equipment. Learn about the wonderful world of stone-grinding grains on one of their free factory tours. 
• The Maryhill Museum of Art. While not technically located in Portland (it’s a 2-hour drive away in a small Washington town) it’s worth the drive for art-lovers! 
• The Oregon Zoo is cute– the sea otters, bears, black rhinos, elephants, the whole 9 yards. They have lots of quirky animal-themed programming throughout the year, too. 
• While not technically located in Portland, Oregon, the Gordon House— the first home designed by Frank Lloyd Wright– is located about a 1-hour drive south of the city in Silverton, Oregon. It’s worth the day trip to visit, especially if you’re an architecture buff! The house is located next to an 80-acre botanical garden, as well, which is lovely in spring and summer. 
• Portland Bee Balm is a cool local product to buy as a souvenir. 
• Love Hive and The People’s Yoga are great places to do yoga in Portland. Meanwhile, just outside of Portland in what is technically Hillsboro, Oregon, Portland Goat Parties hosts adorable Baby Goat Yoga and Baby Goat Therapy sessions that make animal lovers swoon.
• Cool local spas include Everett House (for excellent massage therapy and an amazing saltwater hot tub + steam room), Common Ground (another great soaking pool with spa that offers acupuncture and naturopathy), and Loyly (which offers traditional Swedish massage and uber-relaxing dry saunas). If you’re looking for some relaxation in Portland, saunas are a popular local way to do it!  

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Related: Traveling around the Pacific Northwest? Read our Insider Guides to Seattle and Vancouver next.

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