Stunning views. A vibrant food scene. The most incredible bookstore.

This just about sums up what people had told me before I’d ever set foot in Portland, Oregon or any of its surrounding areas. I’d been wanting to visit the City of Roses for years, but plans with friends never quite worked out. 

Then, last May, I had the opportunity to present at a conference in Skamania, Washington – just over the Oregon border. Afterward, I squeezed in some time to explore both Portland and its natural spaces, but knew I had to come back one day to see more. 

This past Memorial Day weekend, I returned – and loved experiencing the city at a more relaxed pace. Here are my highlights, lowlights, and overall reflections on the city of Portland and its nearby attractions. 

Highlights

Columbia River Gorge Highway

There’s nothing like driving along an everyday-looking highway, only to find yourself suddenly surrounded by jaw-dropping scenery. When I first visited the Portland area, I had no idea my drive to Hood River would take me along the Columbia River Gorge, so the views came as a complete surprise. This drive was by far the highlight of that trip, so I had to make sure to drive it again.

Between the blue lake and its islands on one side and the tree-lined mountain landscape on the other, you’ll want to capture every moment of this drive.

Mount Hood

Seattle has the Space Needle. San Francisco has the Golden Gate Bridge. Portland has Mount Hood.

There’s something magical about this massive, snowcapped mountain suddenly appearing as you drive through the region.

For the sake of time, my partner and I didn’t visit Mount Hood directly – we simply looped around it from Sandy to Tamanawas Falls and Multnomah Falls. Still, the mountain views were spectacular.

One thing to note: Mount Hood is not the only peak you’ll see in the area. If you don’t know that, then you – like me – will momentarily think Mount Hood truly is magical as you’ll see mountain peaks in just about any direction you turn! Chances are, the other peaks you’re probably seeing are Mount Adams and/or Mount Saint Helens.

Powell’s City of Books

Are you the kind of person who needs to be dragged out of bookstores? Same. Whether that’s you or not – you’ll need to stop by Powell’s City of Books. It’s easily the number one attraction in Portland.

This four-story bookstore takes up an entire city block on Burnside Street in Portland’s Pearl District downtown, making it the largest independent bookstore in the world.

I’ve visited some pretty amazingly large and Instagrammable bookstores – mainly The Strand in New York and LA’s The Last Bookstore – and while they’ve been a joy to visit, Powell’s is by far my favorite. I love that it’s an unassuming, no frills bookstore – it looks more like a warehouse at times – and houses books on just about any subject you can think of.

The only downside? Eventually, you have to leave.

Tamanawas and Multnomah Falls

Ever since I drove Maui’s road to Hana, I thought I’d seen enough waterfalls to last a lifetime, but Oregon proved me wrong. The state is full of lush trails and falls worth visiting, even if you’re short on time.

Must See: Multnomah Falls

If you only have time for one, go with Multnomah. Located along the Columbia River Gorge, the falls are visible right from the entrance, with an optional (but moderately strenuous) hike to the top. Multnomah does draw crowds, especially from late May to early September when a $2 timed use permit is required – but it’s popular for good reason.

Best Hike: Tamanawas Falls

As highly as I recommend Multnomah for how spectacular it looks, I preferred the Tamanawas hike. Located on Mount Hood’s eastern base, it’s a 3.3- mile out-and-back trail through forest, creeks, and rocky patches. My favorite part? Rounding a bend and suddenly seeing the falls flowing just ahead. While it’s convenient to be able to see Multnomah Falls at the get-go, the hike to Tamanawas Falls feels more earned and the scenery more varied.

Japanese Tea Garden in Washington Park

Located inside Washington Park, Portland’s Japanese Tea Garden rewards its visitors with sweeping views of the city – and, on clear days, Mount Hood. It truly feels like a respite, even with it being located just a few minutes driving distance from downtown. Admission is $22.50, but the garden’s gentle waterfalls, scenic bridges, and peaceful, meandering paths make it well worth it. I loved how the changing terrain encourages you to slow down and take your time walking through the garden.

Lowlights

Lack of Major City Attractions

Portland is a unique city in many ways, one of which being that it doesn’t have many iconic landmarks or attractions. There is no Statue of Liberty or Hollywood Sign equivalent, so if you’re looking for big city sights or monuments, you might come away from Portland underwhelmed.

It was also challenging for my partner and I to find a tour of the city that intrigued us. Most focused on day trips to natural spots like Mount Hood or Multnomah Falls. The in-city options—like Willamette River cruises or visiting Pittock Mansion—didn’t promise much in terms of local history. We usually love city tours for the storytelling, but Portland felt more rooted in nature than narrative history.

One regret? Not taking a food tour. Portland’s food scene is one of its biggest draws, and while we ate well on our trip (we really enjoyed The Screen Door and Rangoon Bistro), I left feeling like there was so much more to try.

That being said, Portland more than makes up for its lack of traditional landmarks and exciting history with its incredible green spaces – even in the midst of the city itself. While most cities are considered “concrete jungles,” Portland is lush in greenery, from Washington Park to the leafy neighborhoods in Eastside.

Drug Use 

This is a difficult topic – and I don’t claim to be an expert – but I want to speak honestly about my experience.

Though Portland’s reputation still includes great food, Powell’s Books, and gorgeous hikes, media coverage also frequently highlights the city’s drug and homelessness crisis, particularly since the state decriminalized small amounts of hard drugs in 2020. I’ve known people who have chosen to forego their Portland trip entirely purely based on coverage of the issue.

On my first visit, I didn’t notice much. This time, though, the city’s drug and homelessness problems were harder to ignore. When passing through Old Town, we witnessed hordes of people on both sides of the street clearly struggling with substance abuse and homelessness. In the Pearl District, we witnessed shouting, car alarms and shattered car windows, and felt general unease.

Most of our visit felt safe and peaceful, but that experience downtown was jarring. Being from the Bay Area, I’m no stranger to these issues—San Francisco’s Civic Center and parts of the Mission feel similar—but the unfamiliarity of Portland made it harder to gauge how widespread the problem was.

It should be known that, as of September 2024, Oregon passed a law to recriminalize hard drugs, but the long-term impact remains unclear. Some feel that visible drug use has decreased, but it’s still too soon to tell.

My Takeaway 

Oregon’s beauty is underrated. Of all the places in the U.S. I’ve visited, it’s easily in my top 5 for nature views. The Columbia River Gorge, Mount Hood, and the area’s many waterfalls have my heart. 

The city of Portland itself has left less of a personal impact, but is by no means a least favorite. Powell’s is my all-time favorite bookshop and Washington Park’s sprawling green beauty makes it one of the best U.S. city parks I’ve explored. 

Portland’s drug crisis is real and visible. I wouldn’t describe downtown Portland as a place I’d leisurely stroll through—but that’s just one part of an otherwise positive experience. Locals were kind, families were out walking dogs, and much of the city felt calm and welcoming.

It’s easy to get caught up in a “single story” about a place—something I know well living in the San Francisco Bay Area. Tell someone you’re from SF and you’re bound to hear a snarky comment about the city’s problem with homelessness.

These criticisms are often valid—but they’re not the whole story.

I hope this post gives you a fuller picture of Portland. Yes, the city has challenges, but I find it hard to think of a city that doesn’t. If in doubt, know that Portland’s food, natural beauty, and world-class bookstore are well worth your time.

Have you been to Portland? I’d love to hear your list of highlights and lowlights – or, if you’re planning your first visit, what you’re most excited to see!