Portland, Oregon: Our Travel Highlights
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You know when you’ve heard so much about a place that it’s nearly mythical in your mind? Well, Portland was one of those places for me. The city had achieved legend status in my mind before I ever set foot in it, what with friends raving about the eclectic scene time and time again. Feeling a little daring with COVID antibodies in our immune systems, we booked our first domestic air travel in a looong time to our neighbors in the North, partly because a short flight for a long weekend away seemed like a good way to test the pandemic travel waters but mostly because we had been waiting to make this trip foreverrrr. And boy, did Portland live up to the hype! If you never left the city at all, you’d have a perfectly good time eating, shopping and in general, living it up. But take my advice and add a couple of roadtrips beyond the city’s borders and you will rave about Oregon until the end of time, just like I am.
Our short but sweet 3 day itinerary took us to Oregon’s coast, the famous Columbia River Gorge and the city’s main attractions. I hope this recap inspires you to visit the City of Roses if you haven’t already, or to revisit with fresh eyes if you have.
Day 1 The Oregon Coast
I will go without being asked to a culturally rich city any day of the week, but I will do it even quicker if it’s a culturally rich city near the coast like Portland is. Having mapped a full day along the famed Oregon coast for ourselves, we got ourselves buzzed on some strong, strong Portland craft caffeine before embarking on the first roadtrip of our trip. You’ll find the highlights of our route listed below, but here’s the main takeaway- the Oregon coast is SO much more than Cannon Beach! As much as we loved that first iconic destination, some of the other quieter stops really did steal our hearts. Go ahead and block out a day on your travel calendar for a day of slow, sweet coast cruising, you won’t regret it!
What needs telling about this recognizable view? 😍 This long stretch of coastline was the first stop on our coastal itinerary for good reason- it gets busy if you wait too long. At around ~9am on a Friday when we got there though, it was relatively uncrowded, moody perfection. The majestic view of Haystack Rock against the foggy skies and silky sands makes for a mystical vibe that is best experienced in person! After a long stroll on the beach, we had a little picnic brunch of our packed Grand Stark Deli sandwiches right on the sand. A pretty perfect start to the day, if you ask me. ☺️
Pro tip- walk up to the tide pools at the base of Haystack Rock for a close-up of some very cool marine life like sea anemones, starfish and more!
2. Manzanita
My personal favorite stop on this route, Manzanita Beach is a hidden gem that’s well worth visiting! The beach itself is a white sand beauty with tall grass bordering the perimeter ala a Nancy Meyers movie set, but there’s also the cutest little beachfront downtown to stroll with lovely boutiques, cafes and pubs.
A quick pullout to enjoy the view and you can be on your way! It was especially beautiful when we visited in the Summer with wildflowers growing rampant on the slopes framing the view. 🥰
6. Tillamook
I had no expectations beyond a scoop of creamy ice cream at Tillamook Creamery, but the home of this giant cheese manufacturer makes for quite an interesting visit! The self-guided tour of the Cheese Factory was fun and entertaining and yes, the planned sugar high delivered as expected. 🍦
We turned back after Tillamook for a dinner reservation in the city, but it is possible to continue on southward for more coastal sights. Also keep in mind that while I highlight the stops we deemed worthy of visiting, there are so many more to explore! Some other well-recommended pins to drop between Cannon Beach and Tillamook would be Garibaldi, Arch Cape and Rockaway Beach among others. And as a final note, the coastal drive was insanely pretty all on its own, meandering through bucolic pastures, blooming woodside and waterfront bluffs, all of which you’ll want to make spontaneous stops for, so have a little extra time handy!
Day 2 The Columbia River Gorge
The most popular roadtrip in Oregon called for a second daytrip from Portland, so off we went in search of some epic Oregon sightseeing! At over 80 miles along and over 4000 ft. deep, the Columbia River Gorge is formed by the meandering course of the Columbia River through the Cascade mountains and forms the state border between Washington and Oregon. The route can be explored in as few or many days as one desires, as the largest National Scenic Area in the country has no dearth of impressive views and fun activities. Our drive covers key highlights that fit into a daytrip from Portland, but if you have more time, it’s possible to plan a more detailed itinerary in this area including epic hikes, biking trails and water-sports among other things.
The Bridge of the Gods & Cascade Locks
We actually didn’t plan on visiting here but I guess technology vetoed that when a wrong dropped pin on Google Maps had us driving across the Bridge of the Gods to the Washington side of the Columbia River Gorge Scenic Area. 😅 Good thing the entire drive was stunning, because what seemed at the start like a frustrating detour to get to our actual destination ended up being a spontaneous few hours of discovering places we wouldn’t otherwise have seen. Starting here meant that we drove off of I-84, crossing over to I-14 in Washington state, so we only saw the OR side after crossing back over Hood River Bridge to rejoin the I-84. In hindsight, this worked out perfectly for us as a loop, covering the entire gamut of sights on both sides of the gorge!
PS. Check out the view below of Mt. Hood from Hood River Bridge on our crossover into OR. 😍 On a clear day, that alone would be worth the extra distance!
2. Hood River
This could be at the end of your itinerary if you’re sticking with I-84 the whole way, and can be a major or minor stop depending on your interests. Outdoor enthusiasts can spends days here alone, taking advantage of all of the river activities the town is famous for. Otherwise, the historic downtown is great for food & drink and shopping, after taking in the views of Mt. Hood from the riverfront.
Driving north for a short while after rejoining the I-84 gets you to this incredible viewpoint at the top of a hill with the the kind of perspective that only height can provide. The wind was nearly toppling us over, but no matter, because the sight before us was well worth it!
We made the spontaneous decision to swing by here and it was so informative! With the sounds of a massive wall of water unlocked in the background, we learned that the dam is one of the world’s largest, provides water to nearly 80% of the PNW, and is a great place to watch migrating salmon and pacific lamprey. 🐟
Sadly for us, Exit 31 with access to this epic waterfall was closed during our visit and we could not see it. 😢 I had saved photos of this beautiful landmark years ago and it was the stop on our route that I was probably most looking forward to. As bummed out as we were, it just means that we’ll have to go back sometime! Make sure to check the website for instructions as the parking situation at the exit appears to need reservations, at last check.
6. The Vista House at Crown Point
This 1917 structure was originally built as a rest stop for weary travelers, an observatory and a memorial to the OG pioneers discovering this route. Today, it is one of the most scenic locations along the Historic Columbia River Highway, providing 360 degree views of the gorge that are unbeatable on a sunny day!
7. Columbia View Lavender Farm
Up north near Hood River, there is an entire area for lilac lovers called Lavender Valley that I would recommend looking up if you’re there in the summer. I had grudgingly dropped it from our itinerary for lack of time, so imagine my delight when we stumbled upon this beautiful little farm right along the way to Vista House! The family-run Columbia View Lavender Farm allows visitors to hand-pick a large bunch of lavender for just $7, take relaxed strolls among the bees and snap as many photos as you would like. Before heading out, make sure to check out their little booth of lavender goodies for gifts and souvenirs. The lavender we picked and brought home made a happy little centerpiece on our coffee table all through summer.
Day 3 The City of Portland
What to do
Explore Downtown Portland
Some downtowns can be sleepy corporate silos, but don’t count downtown Portland among them. On the summer Saturday morning we spent there, it was abuzz with post-lockdown energy. The well-loved Saturday Market was on, music was playing and we toured the local favorites like tourists would- Stumptown Coffee, a Voodoo Doughnuts breakfast, an obligatory photo at the Keep Portland Weird Sign, hippie wares at the Market and people watching on a stroll along the banks of the Willamette River. Having digested the doughnuts, we then booked it to the iconic Powell’s Books, where we only barely managed to not lose ourselves for the entire day- it is a reader’s paradise! There is lots of retail shopping in the downtown area as you’d expect, but in keeping with my inherent talents, we only went to the Buffalo Exchange for thrift finds and left more than satisfied.🙃
Portland Saturday market
Powell’s books
2. Vintage shop in the Hawthorne District
For quintessential Portland i.e. eclectic, bohemian, quirky and free-spirited vibes, all signs pointed to the Hawthorne District. Staring with lunch at Cartopia where the people-watching was as good as the food, we explored Southeast Hawthorne St.by foot after, popping into the many epic vintage shops along the way like Lounge Lizard (funky home furnishings and decor), House of Vintage (I could have spent daysss in the vintage Levi’s section alone!), Jackpot Records and Magpie Vintage (small but true vintage clothing- I’m still thinking about an Edwardian dress I left behind 😍). When re-inforcements were in order, we stopped at the gloriously escapist McMenamin’s Bagdad Theater- one of many historic Portland structures repurposed into a themed pub, restaurants and/or hotel by the local chain- So fun! All in all, an offbeat afternoon right up our alley.🙌
lounge lizard vintage
magpie vintage
3. Golden hour at The International Rose Test Garden
Did you know that Portland is home to the country’s oldest rose test garden? Giving it the moniker City of Roses, the garden features over 10,000 roses and over 600 species! Between May and September when the garden is in full bloom, it is a must visit.💗 On a balmy June evening, we strolled through the beautiful multi-level space and took in the heavenly scent of roses aplenty.✨
Food & Drink
Stumptown Coffee - Portland’s coffee culture is a thing of global renown and fellow bean lovers will want to sample as many of the indie cafes sprinkled around the city as possible. Local giants like Stumptown are a must-try, but also independent cult favorites like Coava Coffee Roasters and Barista are worth visiting.
Voodoo Doughnuts - We’re not even doughnut people and even we stood in line, is how legendary this place is.😅 If you like funky and OTT flavors, go here!
Pine State Biscuits - This was a top rec when I asked on Instagram and boy, was it worth it!
Mucca Osteria- In the heart of downtown PDX, this Italian spot was our choice for our one customary fancy meal on every trip, and it didn’t disappoint!
Blossoming Lotus- A vegan gem! PDX gets 10/10 from us for the sheer volume of vegetarian/vegan restaurants and with the no. of reviews this one had, it had to be great.👌🏽
Petisco- An anassuming place a block from Blossoming Lotus, we only had a drink here. Even so, it was charming and cute!
Cartopia - Food pods, as they’re called in Portland, are a collection of food trucks in a single location and a very popular concept in the city. This particular one is in Hawthorne and knocked it out of the park on food and vibes!
McMenamin’s Bagdad Theater- Weird as it sounds, get the tater tots. SO good.🙊
Lardo - Sandwich lovers, go here! Fun menu, lively vibes, good sammies.😋
Grand Stark Deli - Tucked into the lobby of our hotel, the Deli was just a convenient stop at first to get a packed picnic lunch for our roadtrips, until we became regulars because the food was just that good. Their menu includes Katz’s Deli which is just… IYKYK.🤤
Stumptown coffee
McMenamin’s bagdad theater
pine state biscuits
grand stark deli
Blossoming lotus
voodoo doughnuts
lardo
cartopia
Where we stayed
Hotel Grand Stark is Pali Society’s recent boutique hotel addition to Portland’s Central Eastside and checked all the boxes for us- locally invested, designed with character, in a good location and affordable. We were so impressed with how thoughtfully appointed the rooms were (Diptyque suds, Smeg appliances, noise cancelling earbuds, etc.), the service was great and parking was a lot cheaper than most hotels downtown. And just to repeat myself, a pitstop at Grand Stark Deli on the way out was warranted nearly every day. All in all, this was a hotel stay we enjoyed, so I highly recommend!
That’s a wrap on my Portland recap! If you made it here, thank you for reading. I hope our itinerary helps plan your own very, very soon.🤗
Have a great week ahead!
XO Sushmitha :)
