View of Portland and the Cascade Mountains from Pittock Mansion - 3 Days in Portland, Oregon - 3 Day Portland Itinerary - Things to Do in Portland Oregon

3 days in Portland, Oregon – 10 things to see, do and eat

More than anywhere I’ve ever been, Portland is a city where the food, the people and the atmosphere shine brightest.

Even with all the interesting places we visited and sights we saw, it was during the time spent wandering different neighbourhoods, interacting with wonderfully polite and friendly residents and eating too much delicious food (number 4 on my list especially!) that I felt really got to the heart of the place.

If that sounds like your kind of city too, read on for 10+ ideas to spend 3 days in Portland!

1. Combine history with gorgeous city views at Pittock Mansion

Admission: $12

If you’ve read my blog before, you’ll know I can’t resist a historic house. Add a spectacular panoramic view of the city skyline into the mix and Pittock Mansion became an unmissable Portland destination for me.

The French Renaissance-style home began its life in 1912, built for Henry Pittock, a successful newspaper publisher and owner of The Oregonian. After decades of use by Pittock’s descendants, the house faced decay and weather damage in the middle of the 20th century. The spectre of redevelopment loomed, but the city rallied to save the mansion, raising large sums of money and setting it up as a historic house museum in 1965.

The interior is delightful. We had a look around on our own for a while and then joined one of the volunteer-guided tours for additional context and detail. My highlights were the curved rooms – expressly designed to capitalise on those incredible views – and the airy, white-tiled bathrooms, which featured several elaborate shower designs. One of my favourite shower innovations was a “test” handle, allowing the bather to test the water temperature with a toe on a faucet near the floor. Isn’t that ingenious?

Tip: Be extremely cautious if using Google Maps to navigate to Pittock Mansion. I had actually read myself that sometimes sat nav apps take you to a locked gate, but somehow this entirely slipped my mind when we came to do the drive and it happened to us! Ensure you stay on West Burnside until you see a green sign for Pittock Mansion.

2. Visit a bookstore the size of a city block

By virtue of its size alone, Powell’s City of Books is a book lover’s dream.

“City of Books” is the perfect name for such an enormous, sprawling store. The layout is a little on the utilitarian side, divided into an array of large, colour-coded rooms. But while it lacks the charm and cosiness of some of my favourite book shops, it’s still an amazing place to browse. I especially enjoyed its feature shelves dedicated to store favourites or particular authors or genres.

Tip: Powell’s offers both new and used books. It took me a little while to realise, but the two are fully mixed together on each shelf. Be aware that the prices of used books also vary significantly depending on version and condition; for popular books it’s worth pulling a few copies from the shelf to compare prices!

3. Spot the Simpsons references

Matt Groening, creator of The Simpsons, was born and raised in Portland. If you’re a fan of the animated sitcom you’ll find plenty of noteworthy street names strewn across the map, especially around the Alphabet District. (Apparently Groening had planned to name every character after streets in Portland, but ended up dropping the idea when faced with time pressures.)

Tracking down street signs probably isn’t worthwhile unless you’re a die hard fan, but if you’re exploring the city on foot anyway be sure to keep a look out for Burnside (Burns), Flanders, Kearney, Lovejoy, Quimby et al.

There’s also a sweet illustration of Bart Simpson on the pavement just outside of Lincoln High School, Matt Groening’s alma mater. Here’s a link to it in Google Street View. (It’s easier to spot than normal at this link because someone had coloured it in with chalk in 2016!)

4. Enjoy heavenly doughnuts at Blue Star

It’s fitting that the home of The Simpsons is also home to the best doughnuts I’ve ever tasted. Blue Star Donuts made such an impression that this it’s far and away my top Portland recommendation.

There’s lots to love about their stores, including the design aesthetic and how friendly the servers we had were, but ultimately it has to come down to the doughnuts themselves. And they. Were. Amazing. Over the course of two visits we tried six flavours between us(!), which I think speaks volumes about our immediate and undying love for the little balls of fried dough.

My favourites? The Valrhona Chocolate Crunch and Passionfruit Cocoa Nibs (pictured, above). The O.G. was a close runner up.

Blue Star Donuts vs. Voodoo Doughnut

As you may already know, Blue Star isn’t the only doughnut offering in Portland.

Voodoo Doughnut on SW 3rd Ave is arguably the more famous of the two. Renowned for its quirky flavours, I’d heard that long queues were inevitable, but worth it. After loving the Blue Star doughnuts, I was curious to give its competitor a chance…

Compared to the modern, minimal aesthetic of Blue Star, Voodoo’s approach is exuberantly whimsical. This applies to both the décor and the doughnuts; rainbow-swirled stained glass and walls of colourful merchandise form the perfect backdrop to cabinets full of vibrant doughnuts, many of which bristle with sprinkles, cereal, or crushed cookies.

Fortunately we arrived at a very quiet time of day – there was only one person in front of us in the queue! We got ourselves an eponymous Voodoo Doll (above). It was pretty good, but I’m afraid it suffered by comparison to the Blue Star ones I’d already eaten. Blue Star is the clear winner in my book, but Voodoo get’s a special mention for its multiple vegan options. And for spelling doughnut the British way.

5. Find tranquility at the Japanese Garden

Admission: $16.95

If you’re after somewhere to slow down, get some headspace and admire nature at its most pristine, the Portland Japanese Garden in Washington Park may be just what you need.

It didn’t compare to actual Japanese Gardens, but then I didn’t really expect that it would. Nevertheless it does encompass lots of elements of the ‘real thing,’ including a zen garden, koi pond and babbling streams. There’s also an exhibition space, a café and a couple of shops inside the grounds if you want to extend your visit beyond the garden itself.

One drawback: admission is definitely on the pricey side at $16.95 per adult.

6. Smell the roses at the International Rose Test Garden

Admission: Free

Visiting the International Rose Test Garden in Washington Park is quite the sweet-smelling education; prior to visiting I had no idea so many different rose species were possible!

Though we visited Portland in October, there were plenty in bloom. Initially overwhelmed by the huge variety of rose bushes cascading across 4 and a half acres of garden, our approach was to check the information board on arrival to see which species had won awards. We then picked a few winners in key categories and tracked them down using the map to see if they lived up to their accolades! Beyond that we were happy to just potter around in such a lovely setting, stopping to sample different fragrances as we went.

7. Go thrift shopping

Mostly I don’t shop while travelling, but given Portland’s cooler-than-cool reputation I figured it was a good place to make an exception!

I browsed a handful of both brand and thrift stores and found lots to covet. But in terms of things I was really excited about (and bought), my absolute favourite for selection and low prices was Goodwill on W Burnside Street. The reviews online actually emphasise how expensive it is compared to the average Goodwill but I suppose I either have a skewed perspective on good value, or was just lucky to find some steals!

8. Stroll along the Willamette River

The Willamette River bisects the city of Portland, and the 12 bridges that span it are the source of one of Portland’s many nicknames: Bridgetown.

After a day spent exploring the city, we headed north to The Fields Park for a view of the Fremont Bridge (top image, above), and then wandered back along the river in the pretty golden hour light. With only a few runners for company, it was a really pleasant and relaxing walk.

After about 20 minutes we reached the Steel Bridge and decided to cross over into East Portland, mainly to see the views from out on the river itself. While the views were lovely (bottom image, above), I found the path across the bridge surprisingly busy and rushed from a pedestrian point of view. I didn’t feel able to walk at a leisurely pace or stop and take photos without becoming a nuisance to runners, but perhaps that was just due to being there in the late afternoon.

9. Ride the Portland Aerial Tram

Return fare: $4.90

Our main motivation for catching the Portland Aerial Tram was to get more views of the city, with relative ease and at low cost. It didn’t disappoint.

The tram is part of Portland’s public transportation system, connecting downtown with Marquam Hill and Oregon Health & Science University (OHSU), and as such the trams run every 6 minutes with a return fare of only $4.90. Though I got the impression the tram is used most often by commuters to the University, as a tourist it affords a great view of the Willamette River, with several of those famous bridges unfurling beneath you, and the Cascade Mountains and Mount Hood beyond.

Fun fact: You may also recognise the Portland Aerial Tram if you’ve seen the movie Leave No Trace (which is fantastic, by the way, I highly recommend it). Near the beginning of the film Will & Tom walk into Portland across St John’s Bridge and catch the tram up to the hospital at OHSU.

Portland Aerial Tram vs. Pittock Mansion Views

In my opinion, Pittock Mansion has the edge here. With a greater height the city truly shrinks back and melts a little more into the sweeping hillsides. If for whatever reason you aren’t able to do Pittock Mansion, though, this is a great alternative way to see Mount Hood, the Willamette River and several of Portland’s many bridges.

10. Indulge with an ice cream at Salt & Straw

Though much of the Portland round ups I read focused on doughnuts, several had glowing praise for another food-related institution: Salt & Straw. The ice cream shop, with several locations across the city, has a reputation for unusual but delicious flavour combinations that we couldn’t resist sampling for ourselves.

The experience was actually really fun, in large part because they allow you unlimited tastings of the various flavours before you make a decision. This was perfect for us because we had no idea what to go for based on the menu alone! Plus we had a lovely, friendly and patient server, who was full of recommendations and extra detail about what we were trying.

I can definitely recommend Sea Salt with Caramel Ribbons, which was the one we settled on. I also enjoyed Almond Brittle with Salted Ganache and Honey Lavender, which gave me immediate lavender farm flashbacks.

Note: We went to the store in Nob Hill, which was my favourite area in Portland to stroll around! Definitely pay this area a visit if you like boutique shopping or people watching.

Bonus recommendations

Weary of city life? If you’ll have access to a car in Portland, I can vouch for the following two very worthy side trips…

11. Drive the Columbia River Gorge

View of Vista House and the Columbia River from Chanticleer Point - Things to do in the Columbia River Gorge, Oregon, USA

Take even a short drive east out of Portland and you’ll be rewarded with the sweeping scenery of the Columbia River Gorge. Head across the I-84 for gems like Multnomah Falls, Chanticleer Point (above) and Vista House.

Mount Hood view from Trillium Lake - Things to do in the Columbia River Gorge, Oregon, USA

Or, if you have a little more time, venture southeast to see the formidable Mount Hood up close. We found Trillium Lake (above) an ideal spot from which to take it in, but there are plenty of great options for mountain views!

12. Cannon Beach and the Oregon Coast

To the west, Portland is only a 1.5 hour drive from the beautiful Pacific Coast. We drove across to Cannon Beach, known for the hulking Haystack Rock (top image, above). We’d also planned to visit Ecola State Park just north of Cannon Beach to do some walking and take in the views, but unfortunately we weren’t able to squeeze it in before heading south.

The route down the coast supplies more beautiful coastal vistas. We ended our drive in the tiny seaside town of Garibaldi to see the Oregon Coast Scenic Railroad, browse some antiques and visit the small local museum. If steam trains and history aren’t your thing, though, you could always head a little further south to check out the nearby Tillamook Creamery for a free, self-guided tour!


Over to you

Have you been to Portland or the surrounding area? What were your highlights? I’d love to hear!

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