As a Portland “native,” I’ve seen the City of Roses go through plenty of changes, transforming from a sleepy and oft-overlooked Northwest port city to a national hot spot for all things culinary—and hipsterish. I’ve walked through Portland’s finest parks countless times, and spent hours curling up amongst the stacks at the massive Powell’s City of Books.
I’ve also seen the city through the eyes of an outsider, coming back recently after years spent abroad, allowing me to rediscover my hometown through fresh eyes. Here’s how I would suggest spending three days in the city for any newcomer who wants to experience a blend of Portland old and new.
Always have a hooded waterproof jacket on hand.
If you only have time for one thing, make it Powell’s City of Books.
Devote your first day to getting familiar with Portland, like a Portlander, by renting a bicycle or heading out to visit some of the city’s famous food cart “pods” on a guided bicycle tour.
In the afternoon, head out on a small-group walking tour in downtown Portland. A variety of options are available, including tours that focus on architecture and parks, the local arts scene, or the weird side of Portland.
If you're itching to take some fantastic photos of the city, then get up early on your second day in town and head out for a sunrise trip on Portland's aerial tram and onwards to two more rooftops in Old Town. After your tour, walk over to Powell’s City of Books, the largest new and used independent bookstore in the world.
No visit to Portland is complete without a trip out to the beautiful Columbia Gorge region, a short drive from town. If you don’t have a rental car or don’t want to deal with finding parking or applying for a summertime Gorge permit, your best bet is to sign up for a half-day hiking tour that allows you the chance to visit the Gorge simply and easily.
In the evening, wrap your Portland visit up with a dinner cruise along the Willamette River aboard the Portland Spirit for beautiful views of the city’s illuminated skyline.