Portland, Oregon, you officially have my heart!
Earlier this month, I found myself on a short getaway to the Pacific Northwest and a city that really knows how to “keep it weird.” The trip was filled with good eats, sweet treats, great sights and even better sounds — all thanks to my favourite bros, the Jonas Brothers.
While I was boarding my flight back home, I realized how quickly I had fallen in love with Portland.
- Getting Around: The downtown area and surrounding districts were super walkable, with countless coffee shops, restaurants, bars and local shops to discover on every block.
- Local Vibe: The people in Portland were some of the nicest I had ever met — shout out to all of the kind strangers who killed it as my personal photographers. 📷
- Ideal Weather: The early October weather was PERFECT for my trip — no wind or rain, just sunshine and a light, refreshing breeze. Hello, fall fashion!
The best part: Many of Portland’s highlights and must-sees can be comfortably packed into ONE day.
If I haven’t already convinced you to book a ticket, check out my 24-hour Portland travel guide below and get ready to discover your next destination.
Staying There
The foundation for any great getaway is a welcoming hotel to call home, so find your way to The Paramount Hotel! This lively boutique property in the heart of Portland’s downtown checks off all the boxes — a prime location, great views, soft pillows, too-cozy-to-leave bed, perfect shower pressure and luxurious toiletries (love you, Gilchrist & Soames). Most appreciated was their incredibly kind staff. Checking in, I was greeted with a sweet upgrade to one of their Double Double Balcony rooms and a care package with some equally sweet treats, including a bag of local artisan Poplandia Popcorn — popped to perfection, of course!
Morning
With a full Saturday to myself, I wanted to get an early start on my exploring. First, I was in need of some satisfying morning fuel. If you’re an avocado aficionado like me, you will have the most divine experience at Kingsland Kitchen — just a short walk away from The Paramount. Settled into a window seat, I ordered their raved-about bacon and avocado sandwich and berry smoothie. Both hit the spot, and then some!
Ready to take on the day, I headed to the Portland Saturday Market. This is a great open-air market by the river with booths selling local delicacies, unique art pieces and fun souvenirs like “Keep Portland Weird” shirts. One booth in particular was even selling beautiful flowers, which stood out amongst the beautiful colours and scents in the area.
Leaving the market, I walked back up the street to the classic Keep Portland Weird sign, conveniently located across from another PDX classic — Voodoo Doughnut. One word: YUM. Trust me, the line goes fast and these donuts are so worth the wait! I picked up the guava colada, which comes complete with a mini umbrella, plus my go-to, a sprinkle donut. Both had me living on cloud nine.
Another local favourite for donuts is Blue Star Donuts, which boasts an equally unique range of flavours like meyer lemon and key lime curd, PB & J, and passion fruit and vanilla cake. If you want to taste test both donut spots on your trip, Blue Star has a shop pre-security at the Portland Airport and I honestly can’t think of a better in-flight snack.
Donuts not your thing? Hope you like ice cream! Portland-based chain Salt & Straw serves up scoops of unique, creamy goodness, including a rotating seasonal menu. I highly recommend their staple flavour honey lavender and the Halloween-themed Mummy’s Pumpkin Spiced Potion. So good!
Afternoon
I dedicated the bulk of my afternoon in Portland to taking advantage of Oregon’s tax free shopping. My first stop was the bookstore of my dreams, Powell’s City of Books. Occupying a full city block and housing over one million books, I think you can pretty much guarantee you will find any and every book you have on your reading list — and then add to it. Powell’s is also just a nice place to get inside and escape, with nine different themed rooms and a spacious coffee shop giving you plenty to see, sip and enjoy.
Powell’s borders the vibrant Pearl District, home to many trendy restaurants, coffee shops (including local fave Stumptown Roasters), and stores. I had great luck at the nicest Anthropologie I’ve ever stepped foot inside, plus admired some beautiful west elm, Patagonia, The North Face and Madewell locations. P.S. I’m still waiting for Toronto to get a full Madewell store — let me know if you’re in the same boat!
Walking to my next destination, I stumbled upon a tiny, hole-in-the-wall shopping strip, Union Way. Three words on the sign were enough to draw me in: Wailua Shave Ice. Anyone who knows me knows I love Hawaii, so randomly finding their signature shave ice in Portland was a sign I was truly living my best life. Their top-selling lava flow shave ice was the best afternoon treat, made with finely shaved frozen purified water, pineapple juice 🍍, Haupia foam, Oregon strawberry purée 🍓, fresh pineapple 🍍 and strawberry 🍓. I definitely need to check out their original location in Kauai, HI next time I’m there!
Evening
Whenever I’m in a new city, I make a point of watching the sunset from a stunning restaurant or bar. Ahead of my trip to Portland, I had heard amazing things about Departure, located on the 15th floor of The Nines, a Luxury Collection Hotel, and atop the landmark Meier & Frank Building. My goodness, was this spot ever the place to be. I enjoyed my signature vodka cranberry out on the patio, taking in the unbeatable views and friendly company. This is the perfect spot to impress a date or travel companion!
After Hours
Although being wrapped up in a warm cocoon is a perfectly nice way to end the night, I like to check out what a city’s nightlife has to offer.
After a few episodes of Seinfeld in the room (my current obsession!), I found my way to the back of the posh Woodlark Hotel and slid into a cozy couch seat at Abigail Hall. The recently-opened upscale cocktail bar and lounge is sophisticated, slick and simply cool, with beautiful decor and cleverly named drinks. The friendly bar staff were happy to serve up their Hibiscus Tom Collins, a guest fave Happy Hour (all day Monday, 3-6 p.m. Tues-Sun) cocktail. Tasting as pretty as it looks, the drink blends gin, lemon, Steven Smith “Big Hibiscus” tea, powdered sugar and soda. As they say, Sip Sip Hooray!
If you’re in the mood for bar hopping, you’ve found yourself in the perfect city.
- Teardrop Bar: A cocktail bar with character in the Pearl District — great bartenders, flavourful drinks, and eye-catching glasses. There’s seriously something for everyone’s taste and the locals love it! Try The Excursions and the Paramour. (Open until 12:30 a.m. every night, and 2 a.m. on Fridays and Saturdays)
- The Upper Lip: This buzzing bar offers a wide variety of local craft beers on tap and in bottles. Come for the drinks, but stay for the bright, airy interior with wood accents, plants everywhere, big windows and a beer ceiling. (Open until 11 p.m. every night, closed Sundays)
- Ground Kontrol: This two-story spot near Portland’s Chinatown has all the features you could dream of — cocktails, beer, snacks, vintage video games and pinball machines plus frequent special events. Go get your game on! (Open until 2 a.m. every night)
- Swine Moonshine & Whisky Bar: Connected to the lobby of The Paramount Hotel, this modern-rustic bar features farm-to-table dishes and an extensive list of custom cocktails, like the Flu Shot (Scotch whisky, beet, ginger, honey, lemon) and Day Tripper (Bourbon, pineapple, house grenadine, lemon, orange bitters). (Open until 12 a.m. every night, and 1 a.m. on Fridays and Saturdays)
Now it’s time to go and enjoy everything Portland has to offer!
Have more questions or want to share your fave PDX spots? Comment below or tweet me @angelamcleanx.
Happy travels xx
