When we say Best of the City, we mean it! Our downtown Portland walking tours are the best way to tell the story of Portland; engaging, well-paced and colorful. It’s a weird 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.
All Best of the City walking tours leave from Director Park, and we keep our groups to 12 or fewer people for intimate, personal experiences. $25.
Best of the City | history of architecture and parks | 10 a.m. and 6 p.m. From cast iron-fronted buildings to the grandly disastrous post-modern Portland Building, much of Portland’s history can be told through the buildings and street layouts; most importantly, the prioritization of parks throughout the city center. How did the city’s early urban planners decide on their layouts? How do modern designers look at the past and plan for the future? Who are the people these streets are named for? What’s with all the roses? It’s not a dry history: full of back-room deals, early deaths and greed; and then there were the hippies! We’ll also discuss the modern rise of radical activists in Portland and how that is intimately connected to the city’s history. Two hours, two miles (3.5 km).
Best of the City | urban art and Pearl District | 1 p.m. 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? With a walk down the 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 the Pacific Northwest College of Art. Two hours, 3 miles (5 km).
Best of the City | weird Portlandia. | 4 p.m. We weren’t the first city to use the slogan “Keep [city] weird,” but we were the first ones to steal it. We’ll walk through Portland’s bizarre and strange past and present, exploring the history of weird icons like Darcelle XV (the world’s oldest drag queen), Voodoo Doughnut (started to “soak up the alcohol” in the Old Town district), and the Burnside Skate Park (started as a rogue unauthorized park and eventually recognized by the city). Two hours, 2.5 miles (4 km).
Book any of the tours below!
Remember: the time you choose corresponds to the tour theme.
– 10 a.m. History of Architecture and Parks
– 1 p.m. Urban Art and the Pearl District
– 4 p.m. Weird Portlandia
– 6 p.m. History of Architecture and Parks