Portland's Best: Self-Guided Driving Tour of Iconic City Sights
Places: 28 POIsDistance: 29.04 miDuration: 1h:55m
Tour #2544
About this English self-guided 1h:55m driving tour in Portland
Welcome to Portland, Oregon—the City of Roses! Today, we’ll guide you through a driving tour that blends the historic, the scenic, and the wonderfully weird sides of this city.
As you follow along, you’ll pass elegant landmarks, lush parks, iconic bridges, and neighborhoods that each tell their own story. Along the way, you’ll hear about Portland’s past, meet some colorful characters, and discover why this city is loved for its creativity, charm, and just the right touch of quirk.
From rose gardens and river views to hidden corners and record-setting oddities, this tour is your chance to see Portland the way locals know it—layered, lively, and always a little surprising.
Portland streets are like a maze — many of them are one-way, and to see all the major highlights, we’ll need to do a bit of looping and crossing back and forth.
In this tour, we’ll cross four different bridges over the Willamette River, to bring you the very best views and experiences. For the best results, please follow the designated route, drive slowly and safely, and listen carefully to the guide.
At one point, we’ll even circle back and drive along the same road for a short stretch before continuing on — that’s all part of the plan to make sure you don’t miss any of Portland’s most interesting sights. So just follow the navigation instructions, relax, and enjoy the tour!
So when you’re ready, start your engine and let’s hit the road. Portland has plenty of stories waiting for you.
Distance: 0.00mi
, Attraction : Public Square (Recommended selfie spot).
700 SW Broadway, Portland, OR 97205, USA
Pioneer Courthouse Square – Portland’s Living Room
Alright folks, welcome to the beating heart of downtown Portland: Pioneer Courthouse Square, affectionately known as “Portland’s Living Room.” This is where the city gathers—whether it’s for live music, protests, food festivals, or just to sit on the steps and people-watch.
Take a look around and you’ll see more than just a plaza. Those bricks beneath your feet? Over 70,000 of them were individually purchased by Portlanders to help build this square back in the 1980s. Each brick is engraved with a name, so you could spend an afternoon searching for yours—or someone else’s—if you like puzzles.
Don’t miss the Weather Machine—that 33-foot column with a globe at the top. Every day at noon it puts on a quirky show to announce the forecast, complete with trumpets, mist, and flashing lights. Only in Portland, right?
Over there is the famous bronze “Umbrella Man” statue, officially called Allow Me. He’s been tipping his hat and umbrella to visitors since 1983 and is one of the most photographed figures in the city.
The amphitheater-style steps make this space feel like a cozy outdoor living room, and trust me—it fills up. From summer concerts to the annual Christmas tree lighting, more than 300 events are held here each year.
Oregon Historical Society – Oregon’s Story, Unfolded
On your right is the Oregon Historical Society, the keeper of the state’s stories since the late 1800s. Think of it as Oregon’s attic—but way more organized. Inside, you’ll find everything from pioneer wagons and Native American artifacts to historic photographs and quirky relics that shaped life in the Pacific Northwest.
The star attraction is the “Experience Oregon” exhibit, where you can walk through a covered wagon, step into a canoe, or lose yourself in giant panoramic displays that bring the state’s landscapes and cultures to life. It’s interactive, immersive, and a great way to see just how far Oregon has come.
The building itself is right in the middle of Portland’s South Park Blocks, across from the Portland Art Museum, so it fits right in with the city’s cultural core. If you’ve got the time, step inside and take a spin through the exhibits—you’ll leave with a whole new appreciation for the pioneers, dreamers, and innovators who built this place.
And hey, even if museums aren’t your thing, the gift shop here is worth a peek. Oregon-themed books, maps, and keepsakes make for great souvenirs that you’ll actually want to keep.
Tour itinerary stops | Additional places you'll see on this self-guided tour
Place 1Pioneer Courthouse Square – Portland’s Living Room
Place 2Oregon Historical Society – Oregon’s Story, Unfolded
Place 3Portland Art Museum – A Cultural Cornerstone
Place 4Three Kings Historic Landmark Building
Place 5The Benson & U.S. National Bank Building – Broadway’s Showstoppers
Place 6Powell's City of Books - World's Largest Independent Bookstore
Place 7Providence Park – Portland’s Soccer Cathedral
Place 8Washington Park – Portland’s Backyard Playground
Place 9International Rose Test Garden – City of Roses in Bloom
Place 10Portland Japanese Garden
Place 11Pittock Acres Park Viewpoint – The Postcard Shot
Place 12King’s Heights – A Hidden Hillside Viewpoint
Place 13Northwest Industrial District and Forest Park
Place 14Forest Park – Portland’s Green Giant
Place 15St. Johns Bridge & the Willamette River – Portland’s Gothic Beauty
Place 16Cathedral Park - Under the St. Johns Bridge
Place 17University of Portland
Place 18Overlook Park – A View That Lives Up to Its Name
Place 19Lan Su Chinese Garden – A Little Piece of Suzhou
Place 20Ankeny Street & Ankeny Square – Old Portland’s Crossroads
Place 21Mill Ends Park – World’s Smallest Park
Place 22Tom McCall Waterfront Park – Portland’s Front Porch
Place 23Hawthorne Bridge
Place 24Oregon Museum of Science and Industry
Place 25Ladd’s Addition – The Rose-Trimmed Maze
Place 26Lone Fir Cemetery – Portland’s Outdoor History Book
Place 27Burnside Bridge & the White Stag Sign
Place 28Farewell – Until We Meet Again
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Download the app (Android or iOS), purchase the tour (either here on the website, or from within the app).
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UCPlaces acts as your personal tour guide, providing self-guided audio tours fully navigated within our app using GPS-based navigation. You won't need to switch between external navigation apps.
Whenever you approach a point of interest (POI) on the tour, our app will automatically play the relevant audio story at the right time and place.
If you start the tour before reaching the first POI, the app will navigate you to the starting point and then begin the tour.
How is this more convenient than a traditional tour?
UCPlaces offers an innovative and flexible way to explore exciting destinations on your terms.
Here are some key advantages over traditional tours:
No need to commit upfront or purchase in advance; buy a tour only when you're ready to go.
Walk at your own pace.
No waiting for groups; go on your schedule.
Take the tour in your preferred language.
Start, stop and continue the tour whenever you want.
Returning to the same destination? Take the tour again, and again, and again... And bring a friend!
Enjoy preferred prices.
What's included?
A self-guided audio tour taken via the UCPlaces app [Android / iOS (iPhone) / Apple CarPlay].
Tour route map and in-app GPS navigation (via the UCPlaces app).
Audio stories for places visited during the tour.
Apple CarPlay connection (for iOS users); for a seamless driving tour experience.
What's NOT included?
Earphones (highly recommended).
Smartphone.
Any kind of transportation (including tickets and passes).