5×5: Portland

From tattoo studios and donut shops to mountains and beaches, does Portland really have it all?

Often hailed as the quirky little city of the Pacific Northwest, Portland is a place of simple pleasures. With an abundance of microbreweries, vegan brunch spots and signs urging you to “Keep Portland Weird,” it’s easy to see the character and charm this city proudly displays. Oregon’s largest city is the next destination of 5×5: A series where local Free People employees offer up one of their city’s coolest hangs, tastiest bites or best kept secrets. Take a peek into PDX by checking out these recommendations, straight from the locals who know.

Kaitlin Henderson: Visual Manager-In-Training

Cannon Beach – Cannon Beach, OR 97110
Growing up in Southern California means that I’m no stranger to the beach, but there is something so magical about the Oregon Coast – nothing compares to it. One of my favorite places to visit is the lovely little resort town of Cannon Beach. Its main street is lined with coffee shops, antique stores and small breweries. But the best part is that it’s just an hour and-a-half outside of Portland! Fun Fact: The opening scene of the Goonies was filmed there!

Megan Kutter: Manager-In-Training

Donut Byte Labs – 12 SW 4th Ave, Portland, OR 97204
This hidden food cart gem is located right next to Dante’s off Burnside. Voodoo Doughnut line too long? This is the BEST alternative! Their menu rotates daily with bite-sized pieces of heaven.

Jocelyn Bourlier: Stylist

Dog Mountain – State Rte 14, White Salmon, WA 98672
A tough 7-mile spring hike uphill through the Gorge is well worth the trek, if you’re willing to walk on pure sunshine. Over thousands of wildflowers grow each year here and throughout Portland. No rain, no flowers!

Donzelle Richardson: Store Brand Creative Experience Leader based in PDX

Backtalk – 421 SW 10th Ave, Portland, OR 97205
My favorite boutique can be found in Northwest Portland, not far from our local Free People store. Backtalk is the coolest and most beautiful shop, offering both vintage and designer clothing. It’s also great for stocking up on unique jewelry and art by local designers. I pop in here pretty regularly for visual inspiration as well!

Brianna Sas-Ciampoli: Stylist

Icon Tattoo Studio – 813 N Russell St, Portland, OR 97227
Located in the historic David Block building on N Russell St., Icon is home to some of the most talented tattoo artists in PDX. Walk-ins are available most days so, if you are in Portland and want to adorn yourself with some beautiful art, this is the place!

Have Portland secrets to add? Let us know in the comments below! In the meantime, if you’re local be sure to stop by our Portland Free People stores and say hello!

+ Traveling? Check out more 5×5 features here!

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I love the look of Backtalk. Definitely a store to visit!

Charmaine Ng | Architecture & Lifestyle Blog

3 years ago

Great pics! :)

3 years ago

As a new found resident, I have to agree that Portland is a pretty quirky, magical place! Some of my favorite discoveries since being here include: The Arboretum in Washington Park if trees are your thing, Sloan Boutique – locations on Hawthorne & NW 23rd, Laurelhurst Park – a walk from our house and reminiscent of Central Park (same designer), and most definitely – the Gorge! Seek out Multnomah Falls and the Bridge of Gods for a truly beautiful scene. My blog includes more adventures in & around the city, take a peek! Xo

3 years ago

Portland, has so much to offer…how can someone not mention Powell’s Books? The Portland Rose Garden? And since I’m old enough some of the best legal (if you’re over 21) recreational marijuana bars on the West coast! (And for those who deny it, are lying because so many have moved there just because of the very liberal marijuana culture!)

3 years ago

Love Portland it’s been a while since I’ve been there but would love to go back and visit these spots!

Thanks for sharing :)



3 years ago

Definitely check out the Kennedy School. It’s an old school converted into several bars, a hotel, a restaurant, and more. The hubby and I had bourbon and cigars in detention! Also, Homegrown Smoker has the most AMAZING vegan bbq wings I’ve ever had, I could eat those things for days on end. There’s also a local soy jerky, I can’t remember the brand name, but you can buy it in bulk at Food Fight! in the vegan mini mall. Last but NOT least, the Castle Canyon hike. It’s pretty damn difficult, but breathtaking once you reach the destination. Plus, my husband and I didn’t run into another soul out there, so it’s a rare opportunity to experience the blissful soundscape of the mountains without interruption. It was like being on another planet. Can’t wait to visit Portland again!

3 years ago

I’ve lived here for several years now and I’m constantly finding new (to me) spots to explore, eat, and shop.

As for stores:
Schoolhouse Electric
Paxton Gate

Albina Press
Ristretto Roasters
Case Study

Forrest Park
Mt Tabor
I also go on a lot of walks to look at the amazing houses we have in town

Tidbit Food Cart Pod was my favorite but has since been dismantled (RIP) so there’s one in North Portland near St. John’s that’s my new go-to. Cathedral Park (under the St John’s Bridge) is well worth the trip if you’re in that area already.

3 years ago

Never before deals you didn’t know existed can be found at https://dealz.space/