The city’s oldest neighborhood is filled with surprises. Find them all with the help of our handy itinerary.
It wouldn’t be a trip to Portland without a visit to this iconic donut shop, famous for its flashy pink boxes, 24/7 service and imaginative pastries topped with bacon, bubble gum dust or Cap’n Crunch cereal.
Helmed by a former Nike shoe designer and decorated with vintage Michael Jordan memorabilia, this one-of-a-kind coffeehouse doubles as a gathering place for “sneakerheads” and local footwear employees from Adidas, Under Armour and Columbia (to name just a few).
Now that you’re thinking about shoes, pick out a pair for yourself at Portland’s premier sneaker consignment store, where shrink-wrapped Yeezys and mint-condition Air Jordans sell for thousands of dollars. (Hey, it’s tax-free!)
Originally founded as a retailer of Japanese vinyl toys in 2002, this Old Town stalwart now curates a trend-setting collection of emerging local and international streetwear brands, plus a mezzanine packed with rotating art exhibitions and pop-up shops.
Operated by and for skaters since 1976, Cal Skate hyperbolically bills itself as “the oldest skateboard shop on the planet.” Exaggeration aside, the store’s selection of nearly 500 unique decks and skateboards truly can’t be beat.
Ready to refuel? Bite into a Mi Mero Mole taco filled with slow-cooked guisados (stews) like butternut squash or pork adobo, and you’ll swear you’re lunching on the streets of Mexico City.
Frequently named one of the best comic book shops in America, this hip comic headquarters also stocks zines, graphic novels, international art magazines and even new and used vinyl. But wait, there’s more: They also serve as an indie publisher and art gallery.
In 1999, a team of experts traveled to Portland from our sister city in Suzhou, China, to build an authentic, 40,000-square-foot (3716 sq m) Ming Dynasty-style garden. Today, visitors escape the bustle of the surrounding city to admire tranquil pools and seasonal foliage while wandering the grounds.
Pair your visit to Lan Su with traditional Chinese tea service at this authentic teahouse, which features premium loose-leaf blends served alongside classic Cantonese dishes.
The flagship location of celebrated heirloom brand Pendleton Woolen Mills features the company’s complete line of American-made blankets, home goods and woolen clothing, all colorfully patterned with Native American-inspired prints.
Inhale the alluring scent of fresh leather at this family-owned makerspace, where three brothers use traditional Oaxacan techniques to craft bags, wallets, belts and smartphone cases from all American-sourced materials.
Self-proclaimed geeks of all kinds celebrate video gaming’s golden age at this two-story arcade, which boasts nearly 90 classic video games and pinball machines, plus a full-service bar, tasty snacks and live entertainment.
End your evening with glitz, glamour and a bit of risqué humor brought to you by an all-star cast of female impersonators (including Darcelle, the country’s oldest performing drag queen) at the West Coast’s longest-running drag show.