Once a mainstay for hippies and runaways, Portland is now synonymous with high-end eateries, esteemed breweries, and the hip locals that frequent them. But Portland has also famously maintained its cherished oddities and eco-friendly vibe. From retro neon signs and rickety bridges to green hiking trails, bike lanes, and Cascade-mountain views, Portland’s authenticity is central to its appeal as a newly popular travel destination.
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Its Austin-borrowed “Keep Portland Weird” tagline appropriately reflects the vibe of the many counter-culturists, coffee roasters, and marijuana proponents who’ve flocked to it in recent years. And the dozens of historic local theaters, hotels, and bars that have maintained their original character despite the pull of time and new management continue to demonstrate that Portland isn’t just another generic city.
There’s no true science to the madness of this city, which straddles an invisible line between urbanity and nature. But there are certainly some can’t-miss activities. Here are the best things to do in Portland—some of which are (thankfully) even better in the rain.
The Best Things to Do in Portland, Oregon
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Visit Waterfalls
Some of the country's most beautiful waterfalls run through the Columbia River Gorge, a national scenic area perfect for hiking, biking, and leaf-peeping. Multnomah Falls is the tallest and most famous of the bunch, where tourists flock to the forest-nestled Benson Footbridge halfway up the misty falls to get up close and personal with the rushing water.
Hikers, drivers, and bikers make their way through the hilly gorge to get a glimpse of Multnomah, stopping at viewpoints near smaller falls like Bridal Veil, Shepperd's Dell, and Latourell Falls. Heading to the gorge early and in the rain means you'll get the perpetually crowded Multnomah Falls almost entirely to yourself.
The best way to see everything Portland has to offer is by bike and with a tour guide; Pedal Bike Tours Portland offers easy morning and early-afternoon scenic tour options.
Visit Waterfalls
Some of the country's most beautiful waterfalls run through the Columbia River Gorge, a national scenic area perfect for hiking, biking, and leaf-peeping. Multnomah Falls is the tallest and most famous of the bunch, where tourists flock to the forest-nestled Benson Footbridge halfway up the misty falls to get up close and personal with the rushing water.
Hikers, drivers, and bikers make their way through the hilly gorge to get a glimpse of Multnomah, stopping at viewpoints near smaller falls like Bridal Veil, Shepperd's Dell, and Latourell Falls. Heading to the gorge early and in the rain means you'll get the perpetually crowded Multnomah Falls almost entirely to yourself.
The best way to see everything Portland has to offer is by bike and with a tour guide; Pedal Bike Tours Portland offers easy morning and early-afternoon scenic tour options.
Sample the Food Carts and Food Courts
For many, Portland's biggest draw is its food. You'd be missing out if you didn't prioritize the famed local food carts that pop up in public areas like TidBit Food Farm and Garden, nearby Hawthorne Boulevard's Cartopia, and downtown's aromatic Alder Street Food Cart Pod. Most are readily prepared for the frequent rain storms with tents (and sometimes fire pits).
Here's what to do in Portland if you're looking to stay inside on a wet day but still want your quirky food fix: Head for a food court like Pine Street Market. The new space is home to vendors serving dishes and snacks that are just as delectable as Tidbit's vegan cupcake truck and Korean barbecue carts. Pine Street Market's big names include Pollo Bravo for expertly seasoned (and affordable) "Winner Winner Chicken Dinner" with raddichio salad, Shalom Y'all for Israeli Street Food, and Wiz Bang Bar for hand-dipped soft-serve cones or beer floats.
While you're at it, stroll renowned food and shopping areas like Hawthorne and Division, which are lined with shops and award-winning restaurants. Most are across the Willamette River from downtown, and just a short bike ride away via Biketown public bike rentals. Big-name stops include Salt & Straw for artisanal ice cream flavors like strawberry honey balsamic with black pepper, and Cartopia for decadent or savory late-night crepes from Perierra Creperie.
Explore the Pearl District
While visiting Portland, you'll likely find yourself returning again and again to the Pearl District, in the city's downtown area. This is the one of the best places to go in Portland for local-recommended watering holes, cafes, eateries, shops, and entertainment.
Out of towners and locals alike frequent the areas for famous VooDoo Donuts, amuse bouche-inspired plates at Superbite, coffee creations at Heart, brunch at Tasty N Alder, and perusing at Powell's Books—a historic book store that takes up a full city block and has an impressive rare book room.
Find the Best View
Portland's changing cityscape and surrounding landscape includes skyscrapers, hill-top neighborhoods, the distant silhouette of Mount Hood, and a dozen bridges that earned Portland the nickname Bridgetown. The city is home to the nation's oldest vertical-lift bridge, the Hawthorne Bridge, as well as every type of modern bridge technology. To see them all, just find your favorite perch.
The Aerial Tram to Oregon Health and Science University on the city's South Waterfront offers one of the best views of Portland, and it only costs a few dollars to experience. Medical professionals use these cable cars to get to work, and visitors pile in with them to get a prime view of PDX's shipyards, skyscrapers, and the far-off Cascade Mountains.
Pittock Mansion, a museum and the former home of Oregonian publisher Henry Pittock, is also a popular viewpoint—though farther inland. Portland's public gardens, the International Rose Test Garden, is another elevated point of view to consider—assuming you don't mind it being partially obstructed by colorful flowers.
Imbibe
Portland's culinary expertise doesn't end with food—not even close. Enjoying a craft brew or cocktail is one of the best things to do in Portland, and education-focused breweries, wineries, distilleries, bars, and festivals are a large part of the city's food tourism.
One of the nation's oldest brewer's festivals takes place here every year, and food events like Feast Portland and the Bite of Oregon bring visitors from around the world for panels and events dedicated to wine and beer, as well as food pairings. When there aren't festivals, you can still imbibe at famed Distillery Row, the Multnomah Whiskey Library, Teardrop Lounge, urban wineries, and the microbreweries that await around every corner.
If coffee is more your speed, head to local-frequented Coava Coffee shops, Heart Coffee for house-roasted espresso, and Third Wave Coffee Tours for some expert insight. Portland is world-famous for its coffee.
Hike
It's easy to get caught up in food, drink, and entertainment, but don't forget about Portland's pristine nature. One of the best things to do in Portland is hiking in Forest Park, a favorite among locals and visitors for small waterfalls and a supposedly haunted Witch's Castle within the city limits. Mount Hood and glassy Trillium Lake are worth the 50-mile trip outside Portland if you're seeking moderate to challenging day hikes or camping. The Columbia River Gorge's paved roads and short waterfall hikes make for an easy day trip if you're a beginner hiker or biker, too.
Go Back in Time
The "Forbidden City" of Portland still lives on throughout PDX thanks to McMenamins properties. Dozens of historic bars, brew-and-view movie theaters, hotels, music venues, and pubs in Portland and across Oregon have been given second lives that are true to their roots by local brothers Mike and Brian McMenamin. Eighteen of their properties are on the National Register of Historic Places.
These places will bring you back to the times of vaudeville, speakeasies, and nickelodeons—especially Hawthorne Boulevard's Bagdad Theater, which originally showed films and vaudeville in the 1920s, and hosted the star-studded premiere of One Flew Over the Cuckoo's Nest in 1975. The Middle Eastern-themed theater has kept its original misspelled name since opening in 1927.
Back Stage Bar, an aptly named watering hole behind the cinema, once functioned as the theater's dressing rooms, and was restored to include some of its original artwork and tapestries when the McMenamins acquired it in the 1990s. It's one of many opportunities to take in Portland's past firsthand.
Go by Bike
Biking is one of the best things to do in Portland, and an especially great way to explore the city around rush hour. Take out a Biketown public bike at one of the city's many stations, and then conquer Tillikum Crossing—a car-free bridge that's open only to pedestrians, bikers, and the occasional public-transit cable car.
For a guided bike adventure, join Pedal Bike Tours for a historic downtown tour, wine or beer tours, food cart tours, a Columbia River Gorge excursion, or an opportunity to learn about Oregon's legal marijuana on the Portland Pot tour.
Peruse Mississippi Avenue
If you explore just one neighborhood in Portland, it should be Mississippi Avenue. Rousing music venues, bars both seedy and sleek, outdoor patios with fire pits perfect for sipping cocktails, and high-end eateries all converge here, north of the Willamette River, on several square blocks.
By day, the Mississippi Marketplace food cart pod is bolstered by the area's shopping opportunities: store fronts display handmade glassware, pottery, leather goods, vintage clothing, comics, used records, and more.
Take in a Museum
Whether you're an art connoisseur, a science nerd, a fan of oddities and puppets, or obsessed with pioneer history, Portland has a museum for you. Public installations and esteemed art museums make the city something of an arts community, in addition to its already artistic food scene. Science and history nerds can tour a retired war submarine at the Oregon Museum of Science and Industry. Taking in a museum is one of the best things to do in Portland on a rainy day.
The famous Peculiarium does its part in Keeping Portland Weird, as does the local Puppet Museum. For the story behind the city's past, head to the Oregon Historical Society to see the penny that famously decided Portland's name in a coin toss between the city's Boston-based and Portland, Maine-based co-founders. The latter co-founder clearly won, naming the area for his hometown.
More from SmarterTravel:
- 11 Most Impressive Waterfalls in the U.S.
- 9 Best Food Truck Cities in America
- World’s Weirdest Travel Trends, Explained
Associate Editor Shannon McMahon writes about all things travel. She visited Portland, Oregon as a guest of Travel Portland. Follow her adventures on Instagram @shanmcmahon and on Twitter @shanmcmahon_.
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