72 Hours in Portland, Oregon (Spring 2026)

This spring, Jared surprised me with the sweetest birthday getaway to one of my all-time favorite cities: Portland, Oregon. We packed three days full of incredible food, local shopping, iconic sights, and one very special birthday surprise that had me grinning from ear to ear! From waterfront strolls in neighboring Vancouver to drag brunch, blooming roses, and enough ice cream to qualify as a food group, this trip reminded me exactly why I keep coming back to the City of Roses. :)

Whether you're planning your first visit or looking for a few fresh ideas for your next Portland weekend, here are all of the places we loved during 72 Hours in Portland, Oregon!

72 Hours in Portland, Oregon

Brunch @ La Provence (Vancouver, WA)

We officially kicked off birthday weekend with brunch at La Provence in nearby Vancouver, Washington before making our way into Portland. Their salmon eggs benedict completely lived up to the hype and might honestly be my new default order every time we visit! We also grabbed a couple pastries to enjoy on a waterfront walk afterward, which felt like the perfect slow start to the trip.

Vancouver Waterfront Park

If you haven't made the short drive across the river, add this to your list. We visited Vancouver Waterfront Park for the first time and were immediately impressed by the miles of walking paths, gorgeous Columbia River views, public art, and peaceful atmosphere. It's the kind of place that makes you want to linger a little longer with a coffee (or pastry) in hand.

Dinner @ Kayo's Ramen Bar

Every trip deserves at least one "we have to go back" restaurant, and for us that's Kayo's. We discovered this Williams District gem a couple years ago and have loved it ever since. The ramen is outstanding, but if you take one recommendation from me, make it the kimchi fried rice. I'm seriously still thinking about it!

Ice Cream @ Kulfi

One of my favorite discoveries of the trip! We wandered into Kulfi after dinner and instantly became converts. Their South Asian-inspired flavors were unlike anything we'd tried before. The black sesame Oreo and salted caramel with jaggery were both incredible, and the birthday discount certainly didn't hurt either.

Breakfast @ Henry Higgins Boiled Bagels

Bagels were first on the agenda for day two. Henry Higgins serves authentic New York-style boiled bagels, and the seasonal tomato herb bagel with pesto schmear was easily one of my favorite breakfasts of the weekend. We'd planned to enjoy them in the Rose Garden... until Memorial Day weekend traffic had other ideas. More to come on that.

Darcelle XV Showplace Drag Brunch

Without question, one of the highlights of the trip. Jared surprised me with tickets to drag brunch at Darcelle XV Showplace, an iconic Portland institution and an important part of queer history. We'd talked about visiting for years, and it exceeded every expectation. The performers were hilarious, talented, and so welcoming. Easily one of my favorite birthday surprises ever!!

Dinner @ Piattino

Piattino quickly earned a spot on my list of favorite Portland restaurants. Nearly everything is made from scratch, and you can absolutely taste the difference. We started with a beautiful charcuterie board before diving into homemade pasta, pizza, and fresh salad while enjoying one of the loveliest patios of the trip. If you're deciding on one Italian dinner while you're in Portland, make it this one.

International Rose Test Garden

No birthday trip to the City of Roses would be complete without visiting the International Rose Test Garden. Home to more than 10,000 rose bushes, the garden absolutely shines in late spring. We spent the evening wandering through the blooms during golden hour, and it ended up being one of the most peaceful moments of the entire weekend.

Ice Cream @ Salt & Straw

Would it even be a Portland trip without Salt & Straw!? We wrapped up our birthday celebrations with one final scoop before heading back to the hotel. It's touristy for a reason - and still completely worth the stop.

Shopping in the Pearl District

The Pearl District continues to be one of my favorite neighborhoods to wander. This trip, I visited Oblation Papers and immediately understood why fellow stationery lovers rave about it. Between beautiful papers, washi tape, stickers, and journaling supplies, I could've spent hours there. We also browsed Blick Art Materials, stopped into Hello From Portland for locally made gifts and souvenirs, and later made a quick trip over to Nob Hill to visit Paper Source before heading home.

Lunch @ Screen Door

Screen Door had been sitting on my Portland bucket list for years, and I'm so happy we finally made it. We lucked into the last patio table before the kitchen closed and enjoyed another phenomenal eggs benedict (apparently this became the unofficial food of the trip), while Jared went with their famous chicken and waffles. We'd gladly order both again.

Dinner @ In-N-Out & Burgerville

Our final dinner was a tale of two burgers. Jared requested In-N-Out, where he finally perfected how to order everything Animal Style, while I couldn't leave PDX without one last Burgerville fix! Their chipotle mayo will forever have my heart. We enjoyed our burgers on the rainy drive home through fog-covered mountains that looked straight out of a movie - a perfectly PNW ending to an unforgettable birthday weekend.

Three days somehow felt both incredibly full and far too short. Portland continues to surprise me every time we visit, whether it's discovering a new favorite restaurant, stumbling into an unforgettable local shop, or simply slowing down enough to appreciate the little moments. Until next time, City of Roses! :)