When we launched Road Unraveled in mid-2014, the very first article we published was about my hometown of Portland, Oregon. The post idea came from the very same motivation Stephanie and I had to start Road Unraveled in the first place: to share travel tips and, hopefully, encourage people to travel and enjoy their vacation time. After I moved to the east coast from Portland in the mid-2000s, I had lots of friends and co-workers ask me for recommendations on what to see and do when they visited Oregon. I put together a list of my favorite spots, and eventually that list was transformed into an article for our website.

Although a lot of what I wrote back in 2014 still holds up and make for great recommendations today, Road Unraveled has grown and changed—and so has our style and commitment to providing in-depth articles that inform and inspire. If my east coast friends and colleagues were to ask me for recommendations now, my tips would be a little different. That’s why we decided to share a fresh, updated article that includes some of our old favorites and incorporates some new ones.

Narrowing down the most interesting things to do in Portland is a difficult task—that is true for any city. I grew up in Portland and graduated from Portland State University, but a lot has changed since I moved to the Washington, DC area almost two decades ago. These days, our return trips are usually focused on visiting with family and friends or checking out different parts of the state, which often leaves us with no more than a weekend to spend in the city itself. That’s why we’re excited about this article: it’s a few of the can’t miss destinations you should have on your list if you only have a weekend to spend in Portland.

Portland is an incredible city to visit, and it offers a great mix of famous locations and up-and-coming spots that are new to the scene. Here are some of our favorite places to visit when we have a weekend in Oregon’s Rose City.

Things to Do in Portland, Oregon

Portland is full of interesting things to see, and you’ll have no trouble finding fun ways to pass the time and cool locations for Instagram photos. If you only have a couple days in Portland, be sure to check out these places around town.

► Bart Simpson Etching

Located at the corner of 18th and Salmon near Lincoln High School, the Bart Simpson etching in an otherwise nondescript sidewalk is a must-see for fans of The Simpsons! Matt Groening, who created The Simpsons, grew up in Portland and used our shared hometown as the inspirations for many characters and storylines. In fact, he named many of the characters after real locations that exist around town. Flanders, Kearney, Van Houten, Lovejoy, Dolph, and Quimby are all real streets in Portland, and you probably recognize those names from the show. A few more Portland locations, like the Terwilliger Curves, Evergreen Terrace, Montgomery Park, Burnside, and even the Columbia River Gorge are also connected to character names or serve as inspiration for locations on the TV show.

It’s a little bit off the beaten path, but if you love the cartoon as much as we do (we even visited the real-life Simpsons house near Las Vegas!) you’ll want to check out Bart’s likeness on the sidewalk. Groening graduated from Lincoln High School in 1972, and when he etched one of his most famous characters into the cement he included ‘Class of 1972’ as well.

One of our favorite clips from The Simpsons is this one, where the family stops by Portland and discovers some of these locations.

 

► Mill Ends Park: Leprechaun Colony

In 1971, Mill Ends Park was awarded the title of world’s smallest city park by the Guinness Book of World Records. The location is at the crosswalk of a busy road downtown, and it’s kind of a blink and you’ll miss it destination—just what you would expect from a leprechaun colony. That’s right—it’s also a leprechaun colony! It sounds like a modern creation, perhaps a leftover remnant from a Portlandia episode, but the park is almost a century old. In the mid-1940s, a newspaper reporter who had just returned from World War II had a view of weeds that were taking over a hole in a median in the middle of the street. He planted some flowers and wrote an article that told the story of the leprechauns who lived in the only colony west of Ireland, noting he was the only one who could see or speak with them and, naturally, was the only one who could give the real scoop on what he termed Mill Ends Park. Although the reporter passed away in the 1960s, the park was officially dedicated in 1976, and it remains a quirky tourist destination as well as a beloved local spot.

► Portland Waterfront photo spot

One of our favorite locations in Portland is the Holman Dock (also known simply as The Dock). Located just south of the Hawthorne Bridge, the Holman Dock is one of the best locations in Portland for panoramic skyline photos. It’s also a great place to just hang out and relax! The dock is open to the public and it’s accessible via the Eastbank Esplanade, a bike and pedestrian path that runs along the eastern side of the Willamette River. Entrance to the dock is free and there is street parking nearby, but you can also park in the nearby OMSI lot for $5. While you’re there, OMSI (the Oregon Museum of Science and Industry) is another great place to visit if you’re interested in a fun science museum with interactive exhibits.

If you’ve ever seen photos of the Portland skyline in books or on TV, there’s a very good chance you’ve seen the view from the Dock. When you spend a weekend in Portland, be sure to stop by for some photos of your own!

► Beverly Cleary Sculpture Garden

Many kids grow up with Ramona Quimby, but you may not realize her neighborhood was based on Portland—and on author Beverly Cleary’s experiences as a child. Cleary grew up in Portland, and she used her backyard as the setting for the popular series—even Klickitat Street, where Ramona’s family lived, is a real place! Today, Grant Park is home to statues of Ramona, her neighbor Henry Huggins, and Henry’s dog Ribsy. There is a small fountain near the statues that is active in warmer weather, which makes it look as if Ramona, Henry, and Ribsy are playing in the puddles. After all, Cleary wrote in her book Ramona the Pest:

“Only grownups would say boots were for keeping feet dry. Anyone in kindergarten knew that a girl should wear shiny red or white boots on the first rainy day, not to keep her feet dry, but to show off. That’s what boots were for—showing off, wading, splashing, stamping.”

A plaque with the quote is part of the park, a fitting tribute to Ramona’s personality and to stories many of us loved when we were growing up—especially Stephanie!

► Rose Test Garden, Japanese Garden, Lan Su Chinese Garden

Portland is known by many nicknames: PDX, Stumptown, and Rip City just to name a few. It’s the City of Roses, though, that is the official and most common nickname. If you like roses, head to the International Rose Test Garden to see more than 7,000 roses on display in the public garden. If the weather is nice, there are even more beautiful gardens to explore in Portland; be sure to stop by the Japanese Garden and Lan Su Chinese Garden, which are both located right downtown.

More Information: PortlandOregon.gov (International Rose Test Garden)
More Information: JapaneseGarden.org
More Information: LanSuGarden.org

► Portlandia

You’ve probably heard of the TV show Portlandia, but did you know there is a statue in downtown Portland that shares its name with the popular TV show? If you only have two days in Portland, the Portlandia statue that sits above the entrance to the Portland Building is one of the most iconic spots to see. The statue is almost 35 tall, and it was inspired by the city’s seal, which depicts a woman holding a trident. Interestingly, the statue was created near my new home in Washington, DC before it was sent by boat to Portland and erected downtown. You won’t miss it when you walk down SW 5th Avenue!

► Pittock Mansion

If you are interested in architecture, Pittock Mansion is a must-see stop during your time in Portland. Built between 1909 and 1914, Pittock Mansion is a great example of Victorian and French Revolution architecture and features luxurious upgrades that many homes don’t have to this day: an intercom system, a walk-in refrigerator, and an elevator are just a few examples of the additions included in the Pittock family’s design. Added to the National Register of Historic Places in 1974, Pittock Mansion takes its name from businessman Henry Pittock, who had the house built for his family. Today it is managed by Portland’s Bureau of Parks and Recreation, which offers tours of the property. We like to visit for the incredible city views the property offers. If you’re planning to incorporate some photography into your visit to Portland, Pittock Mansion is a great place to get a terrific photo of the city skyline. On a clear day you might even see Mount Hood in the distance!

More Information: PittockMansion.org

► Cathedral Park

One of the most picturesque parks in the city is Cathedral Park, which is under the St. Johns Bridge in North Portland. The bridge got its name not because of a nearby church but because of the bridge itself, which rises on huge footings that line up to create an image that looks like a cathedral. Visit in the morning, when the sunlight comes through and casts a peaceful glow across the area; the setting reminds us a bit of Polegreen Church outside of Richmond, Virginia. There is a parking lot and street parking is usually available, which makes visiting easy. Don’t be surprised if you see quite a few people lining up for pictures; during our visit we saw family photos and even an engagement!

► Keep Portland Weird sign

The unofficial motto of Portland is “Keep Portland Weird,” and you’ll find stickers, shirts, and merchandise with the slogan all over town. If you’re looking for a great photo during your visit, check out the Keep Portland Weird sign, which you’ll find on the side of Dante’s across the street from the original Voodoo Doughnut location. The mural is located on SW 3rd Avenue between Burnside and Ankeny Street, and it’s worth stopping by for a photo or two.

If you’re on the east side of the Willamette River, check out the original Keep Portland Weird sign at the place where it all began! The owner of Music Millennium adopted the slogan from Austin, Texas and brought it to Portland as a way to promote local business. Located at 3158 E Burnside Street, the sign is proudly displayed on the side of the Music Millennium building. While you’re there, be sure to go into the store and do some shopping; it’s the oldest record store in the Pacific Northwest, and they have an incredible selection of music.

More Information: MusicMillennium.com

► Powell’s City of Books

No trip to Portland is complete without spending time at Powell’s City of Books. Since opening their doors in 1971, Powell’s has packed an eclectic collection of books onto their shelves with genres from fiction to business to social sciences represented. If you’re looking for something specific, there’s a good chance you’ll find what you’re looking for among the thousands of titles available, but the best trips to Powell’s are the ones where you don’t have a title in mind. Spending time browsing the shelves will definitely inspire you to pick up a book or two and learn something new! Powell’s is an independent bookstore, and their focus on treating each customer as an individual with unique preferences and needs is what sets them apart. We love visiting bookstores during our travels (El Ateneo Grand Splendid in Buenos Aires and Livraria Lello in Porto are a couple more favorites!), and there’s a reason Powell’s is included during every trip we take to Portland: it’s always a fun experience!

More Information: Powells.com

► Shop at Sportswear Company Stores

Did you know Portland is home to Nike, Adidas, and Columbia Sportswear? As some of the largest employers in the Pacific Northwest, if you have a friend (or a friend of a friend) with a connection to one of those companies, you may be able to visit a company store. Visiting company stores is not your typical outlet experience: the legendary employee stores often have brand new items at up to 50% off retail prices. If you don’t know an existing employee and can’t arrange a visit, you may still want to check out the retail and outlet stores in the area. The Nike World Headquarters in Beaverton (just outside of Portland) is open to the public, and it’s almost a living museum dedicated to the brand. Check out this video from Nike to get an idea of what to expect, and don’t forget: there is no sales tax in Oregon!

 

► Attend a Sporting Event: Trail Blazers and Timbers

Portland is an awesome sports town and they have some of the most loyal and dedicated fans you’ll find anywhere in the country. I grew up going to Portland Trail Blazers games, and I’m still a huge fan of the NBA team to this day. The team even inspired one of the nicknames for Portland—Rip City—which is credited to the Blazers’ play-by-play announcer Bill Schonely back in 1971. More recently, the Portland Timbers have developed into one of the most successful MLS franchises in the country, and their fanbase is second to none when it comes to dedication and passion.

If you’re visiting Portland and you’re a fan of basketball or soccer, make sure to check the schedules for these teams and try to catch a home game if they’re in town!

Places to Eat in Portland, Oregon

Portland is one of the best food cities in the United States, so it would be a fool’s errand to truly narrow down the best places to eat. You really can’t go wrong; from the enormous variety of food trucks to the world class restaurants, you’re sure to find something tasty during your visit. Here are a few of our favorite go-to places around town (in no particular order!).

► McMenamins Kennedy School (Detention Bar)

McMenamins is one of my favorite local restaurants, and you’ll find a few locations around Oregon and Washington. While the food is always top notch, it’s the beer that stands out. They’re one of the top 50 largest craft breweries in the United States, and they have something for everyone. Our favorite McMenamins is in the Kennedy School, a historic elementary school dating back to 1915 that’s been converted to a McMenamins restaurant. The highlight of the experience is stopping by the detention bar for a pint. It’s a place where drinking on school grounds won’t get you in trouble!

More Information: McMenamins.com/Kennedy-School

► Take a Food Tour

We love to take food tours when we travel because it can be a great way to experience a new city and learn about it through the lens of the food locals eat. If you’re spending a weekend in Portland and are hoping to gain exposure to a few different spots, all recommended by a local, consider taking a food tour! When we visited Auckland, New Zealand, we discovered our tour operator The Big Foody also offers tours in Portland! We can’t recommend The Big Foody highly enough, and we know you’ll love the Portland tour as an introduction to some of the city’s cuisine.

More Information: TheBigFoody.com

► Donuts: Blue Star and Voodoo

Even if you have never been to Portland, you have probably heard of Voodoo Donut. The donut (or doughnut) shop frequently appears on best of Portland guides, and you’ll usually find lines outside the building at their two locations downtown. They’ve even added additional locations in Colorado, Texas, California, and Florida. The menu is full of fun and creative donut varieties with toppings ranging from cereal and bubble gum to the classic voodoo doll featuring a pretzel stake through its heart and raspberry “blood” filling. If your time in Portland will be spent with someone special, Voodoo Doughnut also performs legal and non-binding wedding ceremonies on-site! Weddings at a donut shop may sound odd, but it fits perfectly with the “Keep Portland Weird” motto and could lead to a few good stories and memories!

If you’re looking to get a quality donut with a less touristy vibe, check out Blue Star Donuts. They have eight locations around town, so you will have plenty of opportunities to stop in during your visit to Portland. Blue Star focuses on an artisanal approach to take their flavors to even higher levels. With flavors like Blueberry Bourbon Basil, Passion Fruit Cocoa Nib, Cointreau Crème Brûlée, and Mexican Hot Chocolate you can discover new flavors and maybe even a new favorite donut shop!

More Information: BlueStarDonuts.com
More Information: VooDooDoughnut.com

► Mother’s Bistro

One of our favorite restaurants in Portland is Mother’s Bistro! We rarely visit without incorporating brunch at Mother’s into our list of things to do in Portland. They have the best buttermilk biscuits and sausage gravy that we’ve had anywhere, but you can’t go wrong with any of the menu items. Full disclosure; I am friends with some of the staff here, but that doesn’t influence our opinion of the place overall. If you go, tell them Adam and Stephanie from Road Unraveled say hi!

More Information: MothersBistro.com

► Burgers and Hot Dogs: Roakes and Burgerville

If hot dogs are your thing, hop in your car and drive 10 miles south of downtown Portland and check out Roake’s! This place might not show up on a lot of Portland best-of lists, but it was one of my favorite hot dog stands growing up. Located at 18109 SE McLoughlin Blvd in Milwaukie, Roake’s has been family owned and operated since the 1930s, and they’ve been churning out their signature foot long hot dogs for generations of customers. We’ve had some great hot dogs in places like Bæjarins Beztu Pylsur in Reykjavik, and Ben’s Chili Bowl in Washington, DC, and Roake’s is right up there with some of our favorites. If you’re looking for something a little closer to Portland, check out the second Roake’s location on the Columbia just north of downtown at 1760 NE Lombard Place.

More Information: RoakesTheHotDogFolks.com

California is home to the famous In-N-Out Burger, the regional fast food chain with an epic following. Oregon has their own amazing regional burger chain, and if you’re visiting Portland you’ll want to check out Burgerville during your visit! The chain uses locally sourced products to incorporate local flavors like marionberry and Tillamook cheese from the Oregon Coast into their menu items. They used to have signs that said “inconveniently located for most of America,” and while that is true, with more than 45 locations throughout Oregon and Washington you’ll have no trouble finding a Burgerville during your visit to the Pacific Northwest.

More Information: Burgerville.com

Things to Do Outside the City

As fun and exciting as Portland is, we always recommend renting a car and heading out to explore some of the areas outside downtown if possible. These locations are not far away, and they could all be easily explored within a day if you really wanted to squeeze everything in. If you have a car, consider these locations during your visit.

► Mount Hood and Timberline Lodge

Mount Hood is truly the jewel of the Portland skyline. Located an hour and a half east of downtown Portland, Timberline Lodge sits at the base of Mount Hood and it’s a great destination for a day trip out of the city. Built in the 1930s, Timberline Lodge was used as the exterior for the Overlook Hotel in the movie The Shining, and it has a fascinating history to explore. If you visit in the winter, this is the place to be for skiing, snowboarding, and other winter activities. In the summer, you can enjoy things like hiking, camping, fishing, and alpine slides (similar to what we experienced in the Smoky Mountains).

There are also some beautiful lakes to discover near Timberline Lodge, including one of our favorites; Trillium Lake. The whole area around Mount Hood is the perfect destination if you’re looking to get outside and enjoy nature.

More Information: TimberlineLodge.com

► The Columbia River Gorge

If you’re a frequent visitor to Road Unraveled (thank you!) you may remember us mentioning Multnomah Falls and Vista House in our Washington Wine and the Columbia Gorge article. These two locations each have their own visitor center and history, and their proximity to Portland make them a great addition to your Portland travel itinerary. Multnomah Falls is a terrific scenic spot for hiking or photos, and Vista House is another wonderful spot for some spectacular views of the Columbia River Gorge. With a little extra time, the quick crossing into Washington will connect you to some of our favorite wineries without tacking too much time onto your day.

Our Post: Washington Wine and the Columbia River Gorge

► End of the Oregon Trail

Oregon was the finish line for two major events in American history: the end of the Lewis and Clark Expedition (which can be explored at Fort Clatsop along the Oregon coast) and the end of the Oregon Trail. We all learn about the Oregon Trail in school, and it was one of the most important eras in American History. The trail was part of a mass expansion westward in the mid-1850s, and it ended in the town of Oregon City about 15 miles south of Portland. Today, Oregon City is home to the End of the Oregon Trail, a museum housed in a giant covered wagon-themed building which features exhibits and artifacts that illustrate what life was like for those early pioneers.

More Information: HistoricOregonCity.org

► Willamette Falls

After you visit the End of the Oregon Trail, hop in your car and drive a mile down the road to see Willamette Falls. At 42 feet high and 1500 feet wide, Willamette Falls is actually the second largest waterfall in the United States by volume behind Niagara Falls. There is a great viewpoint at the rest stop on I-205 in West Linn, which also has a plaque with historical information. If you’re looking for a Niagara Falls-like “maid of the mist” experience to get up close, you’ll find a few boat tour companies that offer day cruises between the falls and downtown Portland. We’ve enjoyed the Jetboat tours, which offer great views and share stories that will help you uncover the history of Portland and the sites along the river.

► Oregon Wine Country

Any article about Portland, Oregon would be incomplete if we didn’t mention the wine region! If you’re looking for recommendations for a few wineries that will introduce you to the local wine scene, check out our article about Oregon wine. The Willamette Valley, which is famous for producing some of the world’s best Pinot Noir grapes, is the perfect day trip destination if you want to visit the wineries and enjoy a tasting or two. You’ll find dozens of wineries within a 30 minute drive of downtown Portland!

Our Post: Oregon’s Willamette Valley Wine Region

Where to Stay in Portland

You’ll have no trouble finding high quality hotel options in Portland. Consider the Benson and the Heathman, two of my personal favorite hotels, if you are looking for a great stay in a historic property. They are both conveniently located near many of the popular places to visit downtown.

More Information: The Benson Hotel (Booking.com)

More Information: The Heathman Hotel (Booking.com)

If you are researching other options, there’s a good chance you’ll find a few choices that meet your needs on Booking.com, our favorite site for discovering and booking the hotels we stay in when we’re on the road. Take a look at some of the deals below and see if there is a hotel for you!

Booking.com

Map of Things to do in Portland

We created a Google Map to help outline all the places we mentioned in this post. Hopefully this can be useful to you as you consider your own areas of interest and places to visit around Portland!

 

Visit Portland, Oregon!

With so many fun things to do in town, we know you’ll have a great time during your trip to Portland. Even if you only have a weekend or a couple days to explore, there is a lot to love about the City of Roses.

If you’re still planning or researching some of the fun things to see and do around town, be sure to visit the Travel Portland website for more ideas.

More Information: TravelPortland.com

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