The Perfect 2 Days in Portland Itinerary

It had been 10 years since I set foot in eclectic, weird Portland and I have many fond memories of my visits there. However, Portland’s destination image has taken a major hit because of COVID-19, political violence, and public safety concerns over the last few years. This of course made me want to visit it even more (because I’m weird like that and love the underdog) to see how it’s changed, and how it has dealt with all the tourism blows. I planned 2 days in Portland to go back to some of my favorite places and to see for myself if Portland had lost its mojo.

When I think of Portland I think of its individualism, donuts, creators, food carts, and cute little neighborhoods. Did this Portland still exist? I would find out over the next two days…and even discover some new pieces to Portland I didn’t know existed!

Is Portland Safe to Visit?

Let’s jump right into it. I had a lot of people ask me if Portland was a safe place to visit. Somewhere along the line, Portland went from weird to scary in people’s eyes. It’s really unfortunate because Portland is a cute little city that is full of passion and promise. Sometimes – it’s just a little too much passion I suppose.

I understand how people got the impression that it might not be safe; the past few years it’s been in the news for demonstrations, riots, and homelessness (all things that many cities have struggled with since 2020). To many people, Portland appeared to be the epicenter of chaotic social and racial unrest. The area that was affected the most by this unfortunate image was downtown.

In an effort to dispel this idea Travel Portland ran full-page ads in the major newspapers in the US

It’s true – the only way to really understand what is happening in a place is to go there – so that’s what I did.

Here’s What I Found

A conference brought me to Portland, but I stayed an extra couple of days to just explore and experience the weird, wild Portland that I love. I stayed downtown and while there is definitely a homeless issue (similar to Denver), I still felt safe.

I walked by myself at night (even though some people warned against it) and just stayed alert – as you should do in any city. However, there were also plenty of rideshare options if you didn’t want to walk.

I was sad to see many downtown shops and restaurants closed, but I think every downtown city in the US is having those same issues.

However, my overwhelming observation was that…