11 Things to Do in Portland, Oregon—The Fabulously Weird City (from a Local!)

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Portland, Oregon, wears its wackiness like a badge of honor. There are so many wonderful things to do in Portland, Oregon, and it’s a popular place to visit. 

The “Rose City” revels in its unofficial slogan of “Keep Portland Weird.” Here, you’ll find the world’s smallest city park (452 square inches), the aptly named Freakybutrue Peculiarium emporium of oddities, and the annual World Naked Bike Ride.

Portlanders will eagerly line up for cereal-topped donuts or bone-marrow-flavored ice cream while enjoying everyday pursuits in their city. Locals’ choices include strolling in the city’s parks and gardens and shopping for locally crafted wares at the waterfront’s open-air weekly Saturday Market.

Must-sees in Portland for visitors include Powell’s “City of Books,” the “hidden” Portlandia statue, and 620-foot tall Multnomah Falls (30 minutes east of town). Don’t forget about eating and drinking as well. It’s not a visit to Portland without sampling craft beer or eating at a food cart pod.

Come visit Portland for the liberal hipster scene, the lively and liveable city core, or as a base to explore the dramatic beauty of the western states. However you come to visit, you’ll have no trouble finding unique and fun things to do in Portland, Oregon.

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Portland Sign on the Arlene Schweitzer Concert Hall

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Best Attractions and Things to Do in Portland, Oregon

Portland’s central core is compact, convenient, and chock full of activities. It serves as the perfect getaway home base. All over the city, you’ll find proudly quirky neighborhoods inviting your discovery and enjoyment.

Many come to Portland for a weekend trip, often as a gateway to explore further in Oregon. Ideally, you should have at least a week to fully appreciate the city and surrounding areas. 

Portlanders adore the great outdoors. The city is within 1-2 hours of the Pacific coast, the Cascade Mountains, the Columbia River Gorge and waterfalls, and Oregon’s own Willamette Valley wine country.

1. Discover Downtown Portland

Downtown is the crossroads of Portland, a place where people are always out and about. Mixed-use architecture makes for plentiful storefronts that house quirky boutiques and creative eating options.

Portlanders enjoy and use their city core, and people-watching is often mentioned as one of the top things to do in Portland, Oregon.

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Downtown Portland from Willamette River

2. Explore Pioneer Square

Any list of things to do in downtown Portland probably starts with Pioneer Square. It’s the city’s unofficial central meeting space and a popular place to visit. This brick-lined plaza once was the Portland Central Schoolhouse before becoming a grand railway terminus hotel for many years.

In the 1950s, the square nearly became a parking garage. However, citizens rallied to reclaim it as a public use space to avoid that fate. They bought commemorative bricks imprinted with their names to memorialize it. 

Today Pioneer Square hosts many events throughout the year as well as being a popular lunchtime resting spot. 

Pioneer Square is located here on a map

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Pioneer Square

3. Check Out The Portland Building and Portlandia

Michael Graves designed this controversial Portland Building. This post-modernist icon just received a major facelift. Its gift box aesthetic always stands out in the crowd.

The uniquely pastel pink, yellow, and blue gift box-styled city office structure is far more beloved for being the home base of the Raymond Kaskey statue, Portlandia.

Portlandia is the nation’s second-largest hammered copper statue. It stands 34 feet high, featuring Lady Commerce from our city seal kneeling while holding a trident high in the air.

Very little traffic passes by the statue due to its placement. As a result, she’s often obscured by leafy maples, making her a fun “hidden find.”

The Portland Building and Portlandia are located at 1120 SW 5th Ave, Portland, Oregon

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4. Wander Around the Tom McCall Waterfront Park and Saturday Market

The Willamette River flows through Portland’s center and once contained a seawall and docks on its western shore. Then the 1940s brought the construction of Harbor Drive to the riverfront. 

By the 1960s, a new bridge meant the freeway could be reclaimed as city park space. Today, Waterfront Park extends thirteen blocks along the river’s shore and is used for festivals and by cyclists and rollerbladers.

The northern portion of Waterfront Park is home to Saturday Market, an institution since 1974. It’s always a fun outing and regarded as the best place to find funky and fabulous locally-made arts and crafts. The market runs from March through December and has over 200 regular vendors. 

The Tom McCall Waterfront Park starts around 98 SW Naito Pkwy, Portland, OR 97205, running to around where I-5 crosses the river. The Portland Saturday Market is located here, and it’s held Saturdays from 10 a.m. to 5 p.m.

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Tom McCall Waterfront Park in Springtime

5. See the Pearl District and Northwest Portland

Just north of downtown is the Pearl District. It’s a section of the city that was once warehouses and was repurposed as a bustling, trendy entertainment and retail zone. It’s a great home base to enjoy some favorite Portland activities. 

The Pearl flows east into Chinatown and west into the Nob Hill and Slabtown neighborhoods, which also host unique attractions. 

The Pearl District is located on a map here

6. Browse Powell’s Books

Powell’s Books is a cornerstone of the Pearl. It has occupied a full city block (68,000 square feet) in a converted auto dealership since 1971.

Its claim to fame is that it’s the world’s largest independent seller of both new and used books. They estimate that they have a million volumes in 3,500 sections. 

Powell’s is also a great place for finding unique gift items, greeting cards, and board games. Powell’s Books is located at 1005 W Burnside St, Portland, OR 97209. It’s open daily from 10 a.m. to 9 p.m.  

7. Visit Chinatown

Portland’s Chinatown, established in the  1890s, was the second-largest on the West Coast. It was the area where laborers arrived for railroading, fishing, and mining. Today, much of the city’s Chinese population has moved east of 82nd Ave to form the core of the multi-cultural Jade District.

Chinatown retains about a dozen traditional businesses, including the Ming-dynasty-styled Lan Su Chinese Garden. The entrance to Chinatown is marked by the 38-foot Chinatown Gateway, which depicts 78 dragons and over fifty fantastical creatures.

Both of these landmarks were constructed by working with Portland’s sister Chinese cities of Suzhou and Kaohsiung. 

Chinatown is located on a map here. The Lan Su Chinese Garden is located at 239 NW Everett St, Portland, OR 97209. It’s open every day from 10 a.m. to 4 p.m.

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Portland Chinatown Gate

8. Get Funky at the Freakybuttrue Peculiarium & Museum 

A true piece of Portland weirdness inhabits the edge of Northwest Portland. The one-of-a-kind Freakybuttrue Peculiarium & Museum is, by best description, an art gallery of all things strange and creepy. Where else would you find old-time postcard sets, alien artifacts, and other bizarre gifts?

Freakybuttrue Peculiarium & Museum is located at 2234 NW Thurman St, Portland, OR 97210. It’s open every day from 11 a.m. to 7 p.m. It costs $5 to enter on Tuesdays and Wednesdays and $7 to enter every other day.

9. Wander Around Forest Park

Against the edge of Northwest Portland lies the seven-mile-long stretch of that is Forest Park. It’s one of the largest urban forests in the country. This green oasis covers over 5,000 acres with eighty miles of trails, including the thirty-mile Wildwood. 

Trailheads allow access at many points. Insider’s tip: the entry points furthest from the center of town will be the least crowded. 

Forest Park is located here on a map. It’s open daily from 5 a.m. to 10 p.m. The most popular access point at Macleay Park can be reached by bus, streetcar, and bicycle. Parking is limited, and using taxis/Uber is advised.

10. Don’t Miss Washington Park and the International Rose Test Garden

Washington Park is one of the most-visited attractions in Portland, Oregon. And in fact, it was the city’s first park purchased in 1871. 

With views of the downtown skyline and Mount Hood to the east, the park is a popular getaway any day of the year. Totaling 400 acres, Washington Park includes the Oregon Zoo, the World Forestry Center, and Hoyt Arboretum.

The jewel in the crown of Washington Park is the renowned 4.5-acre International Rose Test Garden. This magical park contains 650 different rose varieties. 

The garden was founded in 1917 to protect roses from World War I in Europe, and it’s the oldest of a dozen such testing sites worldwide. Individual gardens also honor Rose Festival Queens and festival ambassadors, the Royal Rosarians.

Washington Park is located at 4033 SW Canyon Rd, Portland, OR 97221. It’s open from 5 a.m. to 10 p.m. The International Rose Test Garden is located at 400 SW Kingston Ave, Portland, OR 97205.  

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International Rose Test Garden

11. Enjoy the Portland Japanese Garden

For one of the best places to visit in Portland, check out the Japanese Garden. It has over 62 acres of amazing botanical gardens that you can walk around and explore. Many visitors come here every year to these traditional gardens.

There are many different parts to the gardens, including an authentic tea house, beautiful streams, and small walkways that are perfect for photos.

Many people come here to take engagement and graduation photos since there are so many breathing backdrops.

Portland Japanese Garden is located at 611 SW Kingston Ave, Portland, OR 97205, United States. They are open on Mondays from 12 p.m. to 3:30 p.m., closed on Tuesdays, and open every other day from 10 a.m. to 3:30 p.m. Tickets are $19.95.

Things to Do in Portland, Oregon Beyond the City

Rain or shine, Portlanders love to get out and about—around the city and beyond. Portland’s location makes it easy to travel to the beach, the mountains, the wine country, and – even the high desert.

Popular trailheads fill up early on a daily basis in a locale that can be called a hiker’s haven.

Oregon Coast

Heading west from Portland, it’s about an hour and a half drive to the Oregon coastline. Here,  the beaches are fully public access for all to enjoy. 

The Cascade peaks of Hood, Adams, and St. Helens lie to the east within the same seventy miles of the city. On the other side of the mountains is a whole different Oregon—drier, dramatic, and remote.

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Cannon Beach, Oregon Coast

Columbia River Gorge

Portland’s backyard playground is the Columbia River Gorge. It’s only thirty minutes east of the city and contains the continent’s largest concentrations of waterfalls. The star attraction is Multnomah Falls, a whopping 620-foot wonder.

At the base of the falls is a historic lodge that serves as a visitor center and gift shop. A 2.5-mile trail climbs steeply to the top.

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Multnomah Falls

Willamette Valley

Portland also serves as an entrance to Oregon’s famed Willamette Valley wine country, known for award-winning Pinot Noirs. A few pioneering individuals made a bold decision in the 1970s to plant here, based on the latitude and conditions being similar to France’s Burgandy region. 

While Oregon is one of the top five wine-producing states, most producers are delightfully small-scale. The Dundee Hills is ground central for Willamette Valley wine country, with its iconic red, volcanic soil.

The best experiences involve getting off the highway into the rolling hillsides. Taste in the region’s first wine caves at Archery Summit or surrounded by lavender gardens at Durant Vineyards.

The Dundee Hills are reached by way of Highway 99W, an hour’s drive from Portland. Archery Summit is located at 18599 NE Archery Summit Rd., just past the town of Dundee, and Durant Vineyards is at 5430 NE Breyman Orchards Rd., a turn off of NE Mcdougall Rd, just past the weigh station. Opening hours vary seasonally, and reservations may be required, so please check directly for current reservation policies.

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How to Get to Portland, Oregon

There are a lot of options for transportation to get to Portland, Oregon.

Arrive by Land

Portland is a perfect road trip stopover for a journey along the West Coast. Interstate 5 is the freeway running north and south. It runs from Seattle to the north to California to the south. 

Interstate 84 also connects Portland to Boise, Idaho, as it heads eastward. Amtrak follows similar routes with express Cascades services in the Pacific Northwest Corridor, while rapid bus services like Greyhound and Bolt also serve the central city.

Arrive by Air

Portland’s International Airport has been named the country’s “Best Domestic Airport. “ Though it’s best known for those foot selfies on its 80s-Esque carpet (now replaced). However, the tradition continues with the newer pattern.  

The airport is within the city proper and only a thirty-minute light rail ride to downtown. Mt. Hood is usually visible on your approach, and the airport features shops with locally-made products.

How to Get Around Portland

On Foot

Portland has a wonderfully walkable central core with short blocks and without hills. Portland attractions within the downtown area are actually the easiest to visit on foot.

That way, you don’t have to worry about parking or traffic. Plus, the city’s active street life is part of enjoying a stay here. Taxis, Ubers, and Lyfts are easily summoned should you get tired.

downtown portland oregon

By Bicycle

Portland has many well-marked bike routes across the city core and beyond. In fact, it has been named many times as a top bike-friendly city. 

Biketown (a partnership with Nike) provides dockless orange bikes that you can rent for 20 cents per minute. Bikes can be easily loaded onto all forms of public transit to coordinate longer trips.

By Public Transit

Portland is well served by a wide-ranging bus, streetcar, and light rail network called Trimet. This public transit system also extends into the suburbs.

The downtown area has a dedicated bus mall to enable easy changing between routes, and the colorful Portland Streetcar travels along one side of downtown, forming a central loop. 

The Max light rail trains serve the airport, Expo Center, Convention Center, and many major shopping areas.

All travel on Trimet can be paid with reloadable or one-use “Hop” cards. They are available at Max and streetcar station machines or at retailers like grocery stores and minimarts. 

There’s also a phone app, and bus fares can be paid by cash directly. Fares start at $2.50 USD for an adult fare, good for 2.5 hours of travel.

Ways to Get Around That Are Also Attractions

Originally designed to transport workers between two sections of the Oregon Health Science University campus, the Portland Aerial Tram affords a thrilling three-minute ride over the city. 

Board in the newest city neighborhood of South Waterfront to enjoy incredible views. You’ll see Mt. Hood and St. Helens in Washington from the patio at the upper station atop Marquam Hill. Roundtrip adult fares run $5.15 USD.

portland aerian tram
Portland Aerial Tram

When to Visit Portland, Oregon

Portland tends to be synonymous with rain. And yes, the city does see over 160 damp days per year. This moisture that keeps western Oregon green is rarely a steady downpour, though. Most locals don’t bother with umbrellas since the rainfall is often a drizzle that keeps no one inside.

The flipside of the rainy winters is that summer in Portland is amazing. Every weekend has multiple outdoor festivals, and hiking spots are packed from early until late. Highs are usually in the 70s-80s, with low humidity and long hours of daylight. Weatherwise, you can’t beat summer in Portland.

Sunny summers do bring higher prices and crowds. So the best choice to balance all factors might be the transitional shoulder seasons of spring and fall, March through mid-June, and October through early December.

Where to Stay in Portland, Oregon

Portland offers a variety of convenient lodging options in the downtown and other city center neighborhoods. Nightly rates tend to be highest in the peak season (late May through September), though deals can often be found with persistence.

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Hostel and Hotel Descriptions

Hostelers can make themselves at home at the Portland Northwest Hostel, an outlet of Hostelling International. Located centrally in the Pearl, the hotel offers both dorm or private rooms in a five-building “village.” Two kitchens and laundry facilities are also on-site, with public transit available right outside your door. Rooms start at $76 USD/night.

The Eastside Lodge is a revamped former mid-century highway motor lodge and an affordable choice across the river. Lodging here puts you in the heart of the Central Eastside Industrial District- just a mile from downtown- with abundant eateries and nightlife nearby. This stretch of Lower East Burnside has seen a recent explosion of new architecture yet retains its gritty origins. Rooms start at $86 USD/night.

The Inn at Northrup Station is delightfully eclectic, with a relaxing rooftop terrace. The Pearl is compact and bustling, a favorite for trendy eateries and drinking spots. The Pearl is convenient to everything and moderately priced, with many lodging options. Northrup Station starts at $161 a night.

To pamper yourself in luxury, you can’t beat the Nines Hotel, directly adjacent to Pioneer Square. The Nines is housed within a historic building—the former Meier and Frank department store, built in 1909.

It’s elegantly contemporary and known for its exquisite attention to detail. Downtown always feels like people live there (which they do!), with numerous shops and eateries showcasing a vibrant urban culture. Prices start at $235 USD/night.

Where (and What!) to Eat in Portland, Oregon

Eating innovative and locally sourced cuisine ranks high on many lists of what to do in Portland, Oregon. The metro area is surrounded by an “urban growth boundary” that ensures farms are within easy reach of the city.

The surrounding Willamette Valley that once attracted Oregon Trail pioneers is known for its fertile soil and conducive growing conditions.

What this means is that this is a city that loves to eat! Dining is a cherished activity on its own. Perhaps the most visible clue you’re in a foodie haven is all the food carts.

These petite kitchens are organized into pods and properly called carts as they stay in one place and don’t drive about like food trucks.

Food Carts

Portland has around 600 food carts within a couple of dozen pods scattered throughout the city. Downtown pods tend to be more takeaway style.

Pods in other parts of town are often centered around a courtyard with seating and amenities (such as restrooms). Some pods even have a cart serving wine and/or beer!

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Portland Food Carts

Beer & Coffee

Speaking of beer, Portland is a renowned hub of craft brewing- in fact, another nickname for Portland is Brewvana! Hops are grown in plenty in both Oregon and Washington, and the most common style you’ll see around town is a hoppy IPA (India Pale Ale). The best place to partake of local beer is in a brewpub, where often the beer is produced right on-site.

Another beverage you can’t miss in Portland is coffee, with an estimated eighty roasters calling Portland home. Damp winter days lend themselves to a nice cozy coffee break, and the city is dotted with over 2,000 coffee-serving establishments.

And while Starbucks is seemingly on every corner, independent shops are really the best way to enjoy Portland’s free-spirited coffee scene.


Donuts have been associated with Portland since 2003, the year Voodoo Doughnut opened in Old Town. Voodoo’s founders aimed to fill a donut void in the city but also to create something that typified Portland’s weirdness.

A simple pleasure turned into works of art, and donuts are a delicious piece of Portland to grab and take with you.

Portland Restaurant Favorites

Here are some of the best places to eat in all of Portland.

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Barista Coffee Shop, The Pearl

A Brief History of Portland

How’s this for a weird start? Portland may be the world’s only city named by the flip of a coin. In 1845, original land claimants Asa Lovejoy and Francis Pettygrove wanted to name the new frontier settlement after their own hometowns.

The best two-penny flips out of three resulted in the city being named Portland instead of Boston. The new town quickly prospered as an important West Coast port.

By the late 1840s, Portland experienced a time of rapid growth. It was so rapid, in fact, that the city earned the nickname Stumptown. So many trees were cut down so quickly, leaving stumps everywhere. It worked out as they were used as stepping stones in this muddy frontier town.  

In 1905, the growing city hosted a Lewis and Clark commemorative-styled world’s fair.  Twenty miles of roses were planted in the city for this event, earning Portland its nickname as the “City of Roses.” 

Portland boomed in the 1940s with the construction of new dams on the Columbia River and the Kaiser Shipyards, builder of Liberty Ships. By the 1990s, the tech and graphic design industries reached Portland, with giants like Intel and Nike emerging as world leaders.

Today, Portland has become a mecca for artists, entrepreneurs, and foodies. It’s also filled with outdoor enthusiasts—and yes, those who embrace and cherish the wonderful weird style that is the norm.

Why You Need to Spend a Weekend (or more!) in Portland

Wacky, weird, and wonderful Portland is a tourist attraction in itself. There are so many things to do in Portland, Oregon that you may need to become a regular visitor to enjoy them all. Each trip to Portland can showcase a different aspect of this vibrant, eclectic, and eccentric city.

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This post was contributed by Jill Watkins. She is a Portland, Oregon-based travel writer and certified tour guide. A natural explorer who has led groups throughout the western states, Jill believes you can find wonder wherever you might be.

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