Best of the City Small Group Walking tour

All Best of the City walking tours begin at Director Park in downtown Portland, offering intimate group experiences with a maximum of fourteen participants. The tours are designed to provide a personal and engaging exploration of Portland’s unique character, history, and culture, covering a variety of themes and neighborhoods. The Best of the City | The Soul of the City tour delves into Portland’s activism, art, architecture, and parks, highlighting how early urban planning shaped the streets, the prioritization of public green spaces, and the fascinating stories behind street names, historic buildings, and urban development. Along the way, visitors learn about the city’s colorful past, including back-room deals, early urban struggles, and the rise of countercultural movements, all connected to Portland’s modern activist culture. This tour spans approximately two miles and takes around two hours.

The Best of the City | Urban Art and Pearl District tour explores Portland’s artistic evolution, from its first fine art museum to the thriving modern art scene in the Pearl District. Participants discover public art, murals, sculptures, and graffiti while visiting the Pacific Northwest College of Art and learning about the transformation of churches and warehouses into vibrant creative spaces. The Best of the City | Weird Portlandia tour celebrates Portland’s quirky and unconventional side, highlighting iconic local figures, landmarks, and institutions that embody the city’s playful and rebellious spirit, including famous drag performers, Voodoo Doughnut, and the Burnside Skate Park. Both of these tours last around two hours, covering two and a half to three miles, offering an entertaining and informative look at the city’s diverse neighborhoods and culture.