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The Portland Insider was started by a husband and wife team who wanted to share their great city with the world. Our guided neighborhood walks are designed to expose people to what makes Portland so talked about. It's a city with so much that shouldn't be missed, and we don't want you miss it. 

Frequently Asked Questions:

Are these walks just a bunch of boring history?


Nope! Because Portland offers so much we cover a little bit of everything; some architecture, some food, some shopping, some art and, yes, some history. Mostly we see what’s interesting around town on any given day.

How much walking will there be?


About two miles over the course of two hours. That can feel like a long way for some. If you’re worried that it wouldn’t be good for you to be on your feet that long we recommend something like Wildwood Adventures or Portland Explorer to see the city.

What if it’s raining / snowing / foggy / El Nino?

If the outlook does look inclement it can almost always be overcome with a hooded jacket and some sturdy shoes. If the weather looks actively dangerous, we will contact all participants to make appropriate arrangements.

Are children welcome to join?

Yes! Children of all ages are welcome to join our walks as long as they are accompanied by a parent or guardian, and children under 10-years-old are free. Be advised that we often walk through areas that are narrow and may be difficult to navigate with a stroller.

Are wheelchairs welcome to join?

Yes! We’ll do everything we can to accommodate those with special needs, but many of our walks travel through uneven and unpaved areas. If you or any members of your group have special needs please contact us and we can work to accommodate.

Should I bring anything with me?

We recommend comfortable shoes, a warm layer and a bottle of water. Water, food and beverages are often available from shops along the way.

When is the deadline for reserving a walk?

Reservations are available up to 1 hour before the scheduled time.

How many persons can join my tour?

Reservations for any walk are limited to 12 people. If the dates you’re interested in don’t have enough space for your group or if you have an especially large group, please contact us​.

How can I cancel my tour? Is there any cancellation charge?

Contact us​ or reply to your confirmation email with any changes you'd like to make. Reservations may be modified to another day or time for no additional fee. All cancellations are fully refundable up to 24 hours before the reservation, after which a $10 processing fee applies. 

Where do the walks start and end?

Each walk starts in an easy to find public space and will be detailed in your confirmation email.

Is transportation included?

Transportation is not provided before or after the walk, but information will be provided on the best way to arrive beforehand and return afterwards.

Do you offer food or beverage?

No food or beverages are provided, but are available for purchase from stores on all walks except Forest Park.

Can I pay for my tour in cash?

Unfortunately our guides are not able to accept cash for reservations in person. Due to limited reservation space all participants must purchase a ticket ahead of time.

How do I meet up with the guide?


Meet up location information for each walk can be found in your confirmation email. Your guide will be wearing a Portland Insider name tag to identify themselves.

What if I have additional questions?

Contact us​!

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