What to See, Eat, and Do in Portland in Four Days

I am so excited for today’s post because I get to share my favorite stop on our Pacific Northwest road trip: Portland. Not that San Francisco, Santa Rosa, and the redwoods (and also the Oregon Coast and Seattle, which I’ll share soon!) weren’t all amazing destinations; Portland just had something different.

Portland is indeed “weird” but in the best possible way. It’s open to different lifestyles and opinions, boasts supportive communities, and celebrates creativity. The food scene in Portland is unreal and I loved exploring all the different neighborhoods and small businesses. While many cities don’t have the same feel as the rest of their state (Philadelphia is very different from the rest of the more rural Pennsylvania), Portland has the feel and spirit of Oregon.

It’s a city that I feel everyone should visit at least once and here’s what you need to see, eat, and do while you’re in the Rose City.

Where we stayed in Portland

Like most big cities in the summer time, hotels in Portland tend to cost a bit more. If it was in the budget, I would have loved to stay downtown at the highly recommended Ace Hotel. Instead we opted to stay at an Airbnb. It was a cozy studio apartment with on-street parking in , perfect for our needs. Though it was within walking distance to a lot of great restaurants and coffee shops, we were so exhausted after exploring everywhere in the city.

There are so many adorable and unique Airbnbs in Portland and I highly recommend this option when staying in Portland.

What to see and do in Portland

Though I thought I was going to have all the energy that was promised me in my second trimester, yea, that didn’t happen. Plus we’d already been on the road for almost a week. I was TIRED. Portland turned out to be the perfect place to “recover” because we didn’t have to really “do” anything. But we ended up doing a lot of amazing things without really trying.

What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms

Powell’s City of Books

This gigantic bookstore is on every must-see-in-Portland list and it’s for a good reason. There is nothing quite like it in the world. It takes up a whole city block so you can be sure to get lost in there for quite awhile. I think we spent about an hour and a half there. My favorite part of the store was that it’s staffed by people who genuinely love books. I loved the little book recommendation cards they placed alongside the books. I wish I had room in my suitcase for a book souvenir like one of their cute mugs or tote bags. But they do have an online shop so…

Union Way

Right across from Powell’s is Union Way, a shopping arcade with all small shops. This was highly recommended in lots of Portland travel posts. It’s fun to shop there but I didn’t really find anything that caught my eye. If you’re near Powell’s, it’s worth it to pop in but don’t go out of your way.

Shopping in the Pearl District

You can spend a lot of time in the downtown area known as the Pearl District. While it’s easily accessible by public transportation, parking downtown wasn’t terrible and the garages are way more affordable than any other big city we’ve been to.

I loved, loved, loved the shopping. I mean, obviously, but Portland has just the right mix of local shops and a few well-done chain stores. We did pop into Patagonia and I was tempted to pick up a fleece and give camping a try. For like a minute.

If you’re looking for goods by local Portland makers, you have to stop into Tender Loving Empire. They have a few different locations including one in the airport if you’re looking for a last minute souvenir on your way home! I spent a long time browsing through all the things and ended up with a pair of pretty fuschia earrings (accessories are my favorite tiny and portable souvenirs!) and a little stuffed raindrop. The perfect Portland souvenir for our baby! Tender Loving Empire is also a recording company so you can also take home some vinyl from a local artist.

The best part about the shopping in the Pearl District is its all right there. Just around the corner from Tender Loving Empire in the Pearl District was Woonwinkel. It’s a Scandinavian style home goods, furniture, and gifts. I fell in love with these Xenia Taler dinner plates. Finally, another store I loved was Porch Light. They have a beautiful collection of handcrafted goods and a gorgeous display of succulents in all sizes.

Internal Rose Test Garden

Portland is known as the Rose City for a good reason: it’s the perfect place to grow a variety of roses. You can visit the completely free International Rose Test Garden in Portland’s Washington Park. Again, you can find public transportation up there but it wasn’t too tough to find metered parking. The roses are gorgeous, with so many different varieties. I mean, the picture opportunities alone are worth the visit. On a clear day, you get great views of the city and the mountains beyond.

What we didn’t do but it’s on my list next time is to visit the nearby Japanese Garden. There’s also the Portland Zoo which will be great when we return to Portland with kids (still can’t believe that’s going to be a thing…)

Keller Fountain Park

Nestled in the business district of Portland is Keller Fountain Park. Another totally free activity, it’s a really relaxing spot to people watch and listen to the water. Like I said, we took Portland slow so these kind of spots were just perfect.

Portland Aerial Tram

If you want stunning views of Portland in a very cool way then you’ve got to ride the Portland aerial tram. It’s connected to OHSU and is used by commuters to travel between the waterfront and the Marquam Hill neighborhood. It’s one of only two commuter tramways in operation in the U.S.; the other is the Roosevelt Island tramway which I’ve also been on (bonus points!).

It was relatively inexpensive since you need to purchase tickets for the tramway and pay for parking in a nearby garage. But it’s worth it as you soar up and get a glimpse of the Willamette River, Portland’s many bridges, and its neighborhoods. Unfortunately we were there while the smoke from the wildfires was creating hazy conditions but the views were still pretty good.

What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms

Grab a drink at one (or more) of Portland’s many breweries

Craft beer lovers, this city is for you. There are SO MANY good craft breweries all over the city. I would definitely recommend visiting Deschutes Brewery, since it’s centrally located in the Pearl District and it’s a very cool space.

Even though it’s based outside of Portland, Rogue has an outpost not far from Deschutes and its got way more of their beers than we ever get on the East Coast.

One night we ended up hanging out in the garden at StormBreaker Brewing on Mississippi Avenue after delicious tacos at Por Que No. It was such a welcoming and laid back brewery that served up some delicious smelling food. It was also their trivia night so we had a lot of fun sitting and relaxing while trying to answer some insanely hard questions.

Since I couldn’t drink, we didn’t visit half of the breweries we wanted to. Just another reason to go back! When we go back, I definitely want to check out 10 Barrel Brewing, Little Beast Brewing Beer Garden, and Grixsen Brewing.

More shopping on NW 23rd Street, Alberta Avenue, and Mississippi Avenue

Maybe the reason I fell in love with Portland is there are so many shops to explore. Each neighborhood we visited had a whole bunch of really different, really eclectic shops. I honestly didn’t keep track of them all because I was just constantly telling Nick, “Okay, we need to go in this one!” So yup, you may want to pack an extra, empty suitcase for your Portland visit.

Woodblock Chocolate

Sure, it was about 90 degrees while we were in Portland but any weather is hot chocolate weather. Portland has lots of cool things but visiting Woodblock Chocolate was definitely at the top. We saw Woodblock for sale all over Portland and I’d seen it in gourmet chocolate shops so I was really excited to check it out. You can see them roasting and grinding the beans and the best part? Lots of free samples! Oh, and the drinking chocolate is to die for.

Cathedral Park

I always wanted to see the iconic St. Johns Bridge at Cathedral Park. It was a bit out of the way but definitely worth a visit to see this gorgeous suspension bridge. Unfortunately, the soupy, hazy weather meant we only stayed to snap a few photos before heading to grab an iced coffee.

Tanner Springs Park

We definitely embraced the outdoorsy heart of Oregon and visited a lot of parks on this stop! One of my favorite was Tanner Springs Park, right in downtown, in the Pearl District. This park sits tucked in a quiet area surrounded by some high rise buildings. Its situated on a former wetland site and redeveloped in a really cool industrial way.

Where to Eat in Portland

A quick note about eating Portland: this is probably one of the best food cities I’ve ever visited. You can literally get anything you could ever dream of and find things you never expected. Every single restaurant is passionate about what they serve and they make everything to perfection. If you’re love to eat and want to travel, get yourself to Portland.

What to See, Eat, and Do in Portland in Four Days - wear she blossoms

Blue Star Donuts

If you’re going for donuts in Portland, skip the line at Voodoo Donuts and go to Blue Star. Oh my god were these donuts good! There are so many unique and different flavors but go with the O.G., a delicious, fluffy brioche donut dipped in horchata glaze.

Nong’s Khao Man Gai

If you can only eat at one place in Portland, it needs to be Nong’s Khao Man Gai. There’s both a food cart version and a super small restaurant downtown. We opted for the restaurant (this pregnant lady needed to sit down) and were able to sit outside. I ordered the classic Chicken and Rice, which comes with their signature sauce, and Nick ordered the Chicken and Rice with Peanut Sauce. So simple and so amazingly delicious. I would seriously fly to Portland right now for that dish!

What to See, Eat, and Do in Portland in Four Days - wear she blossoms

Pine State Biscuits

Another amazing, can’t-be-missed spot in Portland is Pine State Biscuits. We heard it gets very crowded at breakfast time so we used our favorite hack: go for a weirdly timed lunch! I think we got there around 11:45 and were able to peruse the menu and order with no problem. There are a bunch of different dishes based on their biscuits and honestly, it was the hardest thing ever to decide. I devoured a BLT biscuit and Nick ordered The McIsley, fried chicken with pickles, mustard, and local honey on a biscuit, of course.

What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms

Por Que No

This may have been one of our favorite dinners and we happened to hit up this taco spot on Taco Tuesday! Even though we got a $1 off each of our tacos, they were easily some of the best tacos we’ve had. Again, it gets crowded, so go early or be prepared to wait.

Pok Pok

We heard that Pok Pok was nearly impossible to get a table at so we just figured we’d have to miss this highly recommended spot. Then I wanted to do some shopping on SE Division Street and since it was a hot day (much of this spot is outdoors), Pok Pok was really quiet. We were so lucky because the Northern Thai food we tried here was amazingly good. We ordered their Vietnamese fish sauce wings, Kaeng Hang Leh, a sweet pork belly and pork shoulder curry, and sticky rice. The waiter was incredibly nice and helpful when it came to ordering too so don’t be intimidated!

What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms

Stumptown Coffee

We couldn’t go to Portland without going to Stumptown Coffee. We went to the original location, complete with the Hairbender sign from the hair salon that was originally there. I wasn’t really drinking coffee (thanks, baby) but I had a sip of Nick’s cold brew and it was everything I dreamed of.

Good Coffee

Down the street from that Stumptown is Good Coffee. I am recommending this spot solely based on how kind and awesome the staff was. Whatever pastry I had for breakfast that day was pretty good too.

What to See, Eat, and Do in Portland in Four Days - wear she blossoms

Salt & Straw

Whether it was sweating weather (which it definitely was) or sweater weather, we were going to stop at a Salt and Straw location. We happened to pop in right before a big crowd and ordered a sampler of four of their deliciously creamy ice cream flavors. Oh my god, so creamy and so good!

What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms

Pip’s Donuts

So you may have to wait in line but it’s definitely worth it. Pip’s donuts are tiny, just a bit or two, but they are SO good. We demolished a warm and fresh half dozen between the two of us. And the best part about visiting Pip’s? Their selection of chais! If you choose to sit in (it’s first come, first seated), you can get a sampler of all the chai brewed that day. I had a smoky campfire chai and it was pretty amazing.

Good Neighbor Pizza

We actually went for dinner here because it served as a location on Portlandia. But it had some of the best pizza ever and it was just a nice, relaxed neighborhood restaurant. We also stopped at The Oregon Public House, a nonprofit pub (totally Portland) that supports local charities. They were having a kids’ singalong happy hour and it was just as delightful and as chaotic as you can imagine.

What to See, Eat, and Do in Portland in Four Days - wear she blossoms
What to See, Eat, and Do in Portland in Four Days - wear she blossoms

Portland, I love you and I miss you. We’ll definitely be back!

Next stop: the Oregon Coast!