Our first day in Portland was an overwhelming success. As soon as we disembarked from our Frontier-operated Airbus, the newly renovated airport showed how time had passed since my last visit to the city.

Arching timber ceilings, expansive glass and an unusually open-feeling main concourse welcomed us back into “The City of Roses.” I hadn’t minded the airport in its earlier state. However, this renovation was impressive. There were even living trees inside!

We were in Portland for a four-day weekend over the 2025 Labor Day holiday. The main reason for our trip was a party/quasi-reunion for one of my wife’s childhood friends. We were also going to enjoy the weekend exploring the city.

We visited Portland semi-regularly throughout the 2010s. However, over the past few years, the majority of our friends and family have moved to other places for various reasons, like retirement and new careers. We now have fewer reasons to visit, but I missed the city’s expansive TriMet system, commitment to bicycling, and ample natural space.

At the same time, I had reservations about returning to the city’s downtown area. While I knew that some generalizations about the city are overblown, I also heard from people who lived there and acknowledged Portland’s issues first-hand. This trip was an opportunity for me to see the city and draw my own conclusion about the current state of it. The topic is so polarizing that, truthfully, I’m even hesitant to write about my experience now.

The train ride from PDX to downtown Portland was uneventful. As we walked towards a ticket machine, a helpful TriMet representative explained at the airport platform how the payment system changed since our last visit. Like most transit systems, you now simply tap your phone or credit card against a farebox. On the MAX, these readers are often placed on the platform. Meanwhile, buses and the streetcar often have them aboard the vehicle itself.

It took us about 40 minutes to get to the Old Town Chinatown MAX station aboard the Red Line. I was quickly reminded of how I loved the transit here. The Siemens-built vehicle comfortably delivered us to our destination without the hassle of renting a car or hailing an Uber. Plus, the train’s route alongside a highway showed its’ top speed. We often kept speed with the Saturday-light automobile traffic traveling beside it.

A few stations we passed along the way were under construction, which proved the region’s ongoing commitment to the network. Also, transit security was visible at different points along the way. My $2.80 fare seemed like a great deal.

It would be disingenuous to not acknowledge the city’s visible challenges as well. Some stops along the way reflect Portland’s ongoing struggle with some of these challenges, like the post-pandemic loss of commercial/office occupants, as well as the homelessness crisis. There were a few places between the airport and the convention center where I would feel uncomfortable getting off the train with my luggage. I’ll be the first to admit that I don’t know the specifics about these locations, but it was my first impression.

At the same time, the city’s ongoing revitalization is apparent. Preparation for a large art festival was underway as we walked from the MAX to our hotel, which was the Hampton Inn and Suites in the Pearl District. We passed vibrant restaurants, multiple shops with grand opening signs and people out and about. My overall impression over the weekend was that the city is quickly moving in a positive direction, but with an underlying fragility to it.

We saw the occasional sidewalk tent and a singular orange syringe cap downtown, but we generally felt safe to explore the immediate area around our hotel on foot (although we weren’t out late at night). I noticed that many buildings are unusually fortified, and businesses have much more private security. There are also many street sweepers and we saw law enforcement on patrol on multiple occasions.

For the rest of our first day, we used the streetcar and buses to visit some popular destinations including Powell’s Books (the largest independent bookstore), Elephants Delicatessen (a great place with a diverse menu that also catered our wedding) and Snow Peak’s store/headquarters.

One of my favorite finds of the trip was Portal Tea. Portal is found a short walk from the NS streetcar line and is on the second floor of a historic building. You go up a quaint interior flight of stairs, open a door, and face a wall with an overwhelming number of tea options. The shop has a traditional coffee shop vibe with couches, tables and well-kept plants. It was so unique that we ended up making the journey here twice.

(Author’s Note: Check out the next segment of our Portland adventure here!)