When we say Best of the City, we mean it! Our downtown Portland Oregon walking tours are the best way to get the story of Portland in a few hours; engaging, well-paced and colorful. It’s a complicated city, but it’s a city with stories in every building, park and brick. We can’t tell them all, so we’ve organized our city’s best things in a few different walking tour routes. Young students or teenagers? Reach out to book a school group tour!
Our Art and the Pearl District walking tour will leave from the Portland Visitor Center at 1129 SW Harvey Milk Street in 2026. Prior to that, our Best of the City walking tours leave from the ball-shaped fountain at the NE corner of Director Park, and we keep our groups to 14 or fewer people for intimate, personal experiences. $34.
Best of the City | urban art and Pearl District | 1 p.m. (by request) How did Portland become the first city on the West Coast with a fine art museum? And how did it develop into a hotbed for modern artists like Mark Rothko and Lee Kelly? How has the newly remodeled Portland Art Museum instantaneously transformed the art scene downtown? With a walk down the South Park Blocks and into the Pearl District, we’ll learn how Portland went from a city of ornate churches to gritty artists working out of abandoned warehouses — and then, to today. We’ll talk about public art and sculpture, murals, and graffiti, as well as visiting art cooperatives and the public spaces of the Portland Art Museum.
After meeting at the starting point, we will walk through the Pearl District, learning about its quixotic name and origin that goes far beyond the adoption of the moniker. We’ll meet giant old imposing institutions and the very opposite — early graffiti that we know acknowledge as fine art, and the street art that has been its legacy.
Meet Portlandia, the image personifying our city, and explore some of our most dramatic and influential public sculpture. Learn how much of our city as we see it today has hippies — and those who fought against them — to thank for its richness.
We walk through the South Park Blocks, visiting the plazas connected to museums and concert halls, including the Portland Art Museum and the Oregon Historical Society, where we will explore how Portland’s commitment to a competitive edge started our first art museum and everything that has happened since.
We end at Pioneer Courthouse Square, after about two hours, and about two miles of walking (3.5 km). There are a few gentle paved hills and some stairs that can be avoided — this tour can accommodate wheelchairs and other mobility devices. On days when attractions are open, we will go inside a few of the museums and galleries to see the art that is publicly accessible, depending on group interest.
