Intro to Portland Small Group Walking Tour

4.8 (185)
Portland, US
4.8 (185)
Portland, US
Product photo
Product photo
Product photo
Product photo
Product photo
Product photo
Product photo
Product photo
Product photo
/ Person

Your Product

Select participants
Infant (0-2)
Min: 0 Max: 0
Child (3-12)
Min: 0 Max: 12
Adult (13-99)
Min: 0 Max: 12
You should select a minimum of and a total maximum of
At least one participant is required. Please adjust and try again.

Free Cancellation up to before the experience starts (local time)

Please wait, fetching options!
Join our engaging and colorful walking tour of downtown Portland, Oregon, and uncover the stories that have shaped this weird and wonderful city. From back-room deals and early deaths to the influence of hippies, we'll explore the best and most complicated aspects of Portland's history. Discover how the city became the first on the West Coast to have a fine art museum and how its cultural reputation has influenced the present day. Delve into the soul of the city and immerse yourself in its ever-changing narrative. Our small group tour ensures personalized attention and safety as we navigate the streets, buildings, and parks that hold the secrets of Portland's past. Don't miss out on this captivating introduction to the soul of the city.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • 2 hours - 2 hours 30 minutes
  • Suitable for 1-12 Participants
  • Small Group Tour
  • Guided Experience
  • Discover the stories behind Portland's buildings and parks
  • Learn about Portland's cultural reputation and influence
  • Explore the city's history through architectural choices
  • Visit Pioneer Courthouse Square and its significance to Portland's history
  • Certified guide
  • Gratuities (always appreciated)

Popular Hotels Closeby

More about this experience


Welcome to the Intro to Portland Small Group Walking Tour! Get ready to embark on a captivating journey through the vibrant city of Portland, Oregon. This tour is designed to provide you with an engaging and colorful experience, showcasing the best that the city has to offer. From the fascinating history to the unique stories hidden in every building and park, get ready to uncover the soul of Portland.

What to expect?

During this 120 to 150-minute tour, you can expect to explore the city's most iconic landmarks and delve into its rich history. Starting at DIRECTOR PARK, you'll have the opportunity to discover the fascinating story behind Portland's development and its cultural evolution. Immerse yourself in the captivating tales of early deaths, back-room deals, and the city's influence on racial justice protests. This well-paced tour provides an in-depth exploration of Portland's past, present, and future.

Who is this for?

This small group walking tour is perfect for anyone with a curious mind and a love for immersive experiences. Whether you're a history enthusiast, a culture buff, or simply a traveler looking to uncover the hidden gems of Portland, this tour welcomes you with open arms. From locals wanting to rediscover their city to first-time visitors eager to dive into Portland's unique atmosphere, this tour caters to a diverse range of interests and backgrounds.

Why book this?

Embark on this tour and experience Portland like never before. This captivating journey will unveil the city's secrets and give you a deeper understanding of its past, present, and future. Led by knowledgeable guides, you'll gain insider insights and discover the stories behind the street layouts and architectural choices that have shaped the city. With a maximum group size of 15, you can expect a personalized and safe experience while exploring the unique character of Portland.

Good to know

It is important to note that this tour starts at DIRECTOR PARK and ends at the same location. Conveniently located in downtown Portland, this meeting point is easily accessible by public transportation or by parking nearby. The tour duration ranges from 120 to 150 minutes, allowing plenty of time to explore and soak in the city's atmosphere. Don't forget to wear comfortable shoes and bring along a camera to capture the memories of this unforgettable journey.


Travelers who have experienced the Intro to Portland Small Group Walking Tour have praised its engaging nature and the wealth of knowledge shared by the guides. Visitors have been amazed by the city's hidden stories and the opportunity to explore landmarks such as Pioneer Courthouse Square and the South Park Blocks. Overall, guests have expressed high satisfaction with the tour, highlighting its educational and enjoyable aspects. Don't miss out on this opportunity to discover the captivating history and vibrant culture of Portland!

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Your Itinerary

Director Park

All tours start at DIRECTOR PARK. We'll meet you in the southeast corner of this urban hardscape park, near the intersection of SW Taylor and SW Park Ave. Our meeting spot is across the street from entrance to the Regal Fox Tower. Parking is available on the streets nearby or in lots in the adjacent building. The MAX light rail comes just a block away, at the Pioneer Square stop.

South Park Blocks

Much of Portland’s history can be told through the buildings and street layouts; most importantly, the prioritization of parks throughout the city center. We'll walk through the park blocks and learn why they were laid out this way; and what the park blocks' designer didn't do before he died.

The Portland Building

From cast iron-fronted buildings to the grandly disastrous post-modern Portland Building, we trace our history through architectural choices our city planners made.

Pioneer Courthouse Square

No tour of downtown Portland, or history of the city's relationships with hippies, would be complete without a visit to Pioneer Courthouse Square. From its past as the center of education to the drive to keep out the "dirty hippies," we'll learn how and why this square has never been far from the minds of Portlanders and the city's visitors.



4.8 (185)


Shannon gave us a fantastic tour. In addition to facts, she told us interesting background stories about the places we passed, including some of her own experiences. We were a small group, and she paced the walk well—not too fast, not too slow. Walking is the best way to see city buildings and public art, and we thoroughly enjoyed learning as we walked. Highly recommended for travelers AND Portland residents, who might be surprised to learn new details about their city.


Our guide was terrific. She had such in-depth knowledge and insight into the history and current events of Portland, the time flew by.


Nancy was knowledgeable of some Portland history which was interesting and fun. I have lived in the Portland area for over 30 years and Nancy brought Portland into a whole new light. Thank you Nancy


Shannon was right on time and I can't imagine there is anyone more knowledgeable about Portland. We walked a circuitous route that covered everything big and small. A really great experience.


Nancy was a fantastic tour guide who shared her knowledge about the history of Portland. Before we started the tour, she made sure I was warm enough, so she gave me the hand warmers. The tour went an unique way, because she lived in my hometown Boston, so she cross-referenced our culture/history. Walking was comfortable and even in a rainy condition at the end, I really enjoyed the tour. I highly recommend this tour to everyone.

Michael G

Shannon was a great tour guide. Her knowledge and history of the city was extensive. We’ve done a few walking tours in different cities and she was one of the best. Highly recommended.


Learned a lot of personal history of Portland and Guide. Conversations about sites and general history helped me create a list of things to go see after the tour.


Our guide, Nancy, was GREAT! Very knowledgable and personable. We have already recommended the tour to other folks.


Despite the intermittent rain and a chilly day, Nancy our tour guide, made the tour so interesting that we barely noticed the weather. I booked our group of 6 adults as a way to share more of our city with visiting family. We've lived here for 14 years and thought that a tour would also given us an opportunity to learn more too. Nancy grew up here and has the deep (and sometimes scandalous) scoop of history, and her lived experiences here provided the kind of engagement that you want in a guide. We're still talking about how much we enjoyed this tour and look forward to working with her again for other tours too! Highly recommend.


The tour was great! High energy and so informative! It was a full 2 hours and we came away with great history and an understanding of the city. Otniel was friendly and well versed in the art and history of downtown.
Collected by Evendo & our supplier partners
2024-06-17 20:14