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Pioneer Courthouse Square, Portland

Pioneer Courthouse Square, Portland: Our most recommended tours and activities

Portland, Oregon: Soul of the City Walking Tour

1. Portland, Oregon: Soul of the City Walking Tour

Discover some of Portland's most influential architecture, from cast iron-fronted structures to the grandly disastrous post-modern Portland Building, on this walking tour. Discuss the modern rise of radical activists, and how it is connected to the city’s history going back more than a century. Meet your guide in the center of the city, at Director Park, only a block from the city's Cultural District. 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. Explore how Portland got its nicknames and city layout, how its cultural identity was forged, and where its commitment to racial justice and social progressivism comes from. Be surprised as you find out how the state of Oregon was founded and why. Next, meet Portlandia, the image personifying the city. Learn how much of the city as you see it today has hippies to thank for its richness. End the tour at Pioneer Courthouse Square. On days when attractions are open, you can briefly enter 1 or 2 buildings. Along the way, discover what led to the prioritization of parks throughout the city center, how the city’s early urban planners decided on their layouts, how modern designers look at the past and plan for the future, and who the streets are named after.

Portland: Smart Phone Scavenger Hunt

2. Portland: Smart Phone Scavenger Hunt

Turn Portland into a giant game board on a smart phone operated scavenger hunt of the city, and discover the sights from a new perspective! The interactive hunt combines all the fun of the “Amazing Race” with a sightseeing tour of some of the city’s most historic areas. Let your smart phone guide you past well-known attractions and overlooked gems, solving clues and completing challenges as you go. Start on Pioneer Courthouse Square and continue to the Arts District. See Art Deco theaters and riverside panoramas as you pass sights such as the Portland Art Museum, statue of Portlandia, Ira Keller Fountain Park, and Powells Books, flagship store of the largest independent bookstore chain in the world! The route covers approximately 2.4 miles, and lets you experience Portland’s famous street cars along the way. You can start when you want, and determine your own pace of play. Stop for lunch, take in the sights, or grab a bite at Voodoo Donuts - “the magic is in the hole!” Tours are set at a fixed price for a group versus per person pricing, so this is the perfect city adventure for groups who want to get the best bang for their buck.

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Other Sightseeing Options in Pioneer Courthouse Square, Portland

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What people are saying about Pioneer Courthouse Square, Portland

Overall rating

4.8 / 5

based on 8 reviews

This guide has excellent knowledge of the city and did a great job adjusting for the weather. Her personal bias on political and social matters was very clear. I would have preferred both sides of each story. For example: there was clear criticism of the loggers and 1st developers but without them Portland would not have been the city she obviously loves.

I had a wonderful tour! Our guide did an excellent job of making the history of Portland come alive for me. It’s such a complex and interesting city. Although the weather did not cooperate, she was gracious enough to lead the tour for our group without hesitation.

The walking tour with Rachel was fantastic she has a wealth of knowledge and she was so very personable and just very throuogh in how she communicated the history of Portland. If I were to return I would definitely do this tour again loved it.

Rachel was such an informative and great tour guide. I learned a ton and really enjoyed my time. She answered all my questions so well