City Highlights

• Location: Portland, Oregon, USA

• Population (metro): 2.51 million

• Known for: Largest City in Oregon, International Rose Test Garden, Gateway to the Willamette Valley, Being Weird

• Weather during visit: Mostly Sunny, 26ºC (79ºF)

• Time in Place: 49 hours 39 minutes

Portland is a city that thrives in the in-between spaces. The city is located in the confluence of the Willamette and Columbia Rivers, nestled between the Coast Range and Cascade Range while offering stunning views of each from the steep slopes of the city streets. Even the metro area is in the middle, split between Oregon and Washington. Despite all these middling characteristics, Portland is a city that likes to stand out, and it definitely makes a name for itself. It’s the largest city in Oregon, a Mecca for counterculture, and has a long, storied past going back to the Lewis and Clark expedition. From the heart of the bustling city to the stunning landscapes that lie just beyond its borders, Portland offers a nearly unrivaled connection between scenes manmade and wild.

I visited Portland early in the summer of 2024 with friends as a celebration trip, and the region proved to be a great place to do that. We spent two full days in the area, each one exploring a different aspect. This report will cover the first day, mostly spent in the city of Portland and its surrounding areas, while the next report will include details from our second day exploring the Oregon coastline. These were a very full pair of days, and each one contained a multitude of surprises.

Arriving in Portland

Getting to Portland

While there are still highways in Portland (most notably I-5), there are also plenty of other ways to arrive in the city. Amtrak serves the city via Portland Union Station along three different routes: the Cascades, the Coast Starlight, and the Empire Builder. The Cascades and Coast Starlight services are through running, with Cascades marked as a more commuter-oriented line offering more stops and seven roundtrip frequencies daily between Eugene and Vancouver, BC, while Coast Starlight is a more traditional once-daily long-distance service between Los Angeles and Seattle. Portland also serves as one of the two West Coast termini for the Empire Builder with daily long-distance operations to Chicago. There are also Intercity bus connections to and near Union Station on national carriers like Greyhound, as well as extensive regional bus operations.

The main entry point for visitors to the city, both domestic and international, is Portland International Airport. By far the largest airport in Oregon and the third busiest in the Pacific Northwest, PDX welcomed more than 17 million passengers in 2024. The airport is a large hub for Alaska Airlines with significant presences also by Delta Air Lines and Southwest Airlines. Although primarily focused on domestic operations, the airport does have some international destinations such as London, Amsterdam, and Reykjavik.

The airport recently opened a renovated main terminal, providing travelers with more amenities than ever and looking stunning while doing so. This expansion was not yet open at the time of my visit, but it was notably in the construction phase. From walled-off sections of the check-in area to a slightly disorganized TSA area, and the sounds of drills and hammers echoing through the terminals, the great hall felt years away but it was closer than I had expected, and I hope to return to the airport soon to see it. From what I have seen of it, it looks quite impressive, but I will reserve full judgment for an in-person visit.

When one of my travel partners and I arrived at the airport, we were immediately met with a “Welcome to Portland” sign, always a promising first introduction to a city. There was not much noteworthy about the concourse we arrived in, but there was the famous PDX carpeting running down the corridor. We passed by a few shops and restaurants, though most were closed at 9:30 a.m. on a Monday. The baggage claim area was a bit chaotic thanks to the construction, but once the full group was assembled we were on our way. While I normally take transit from the airport into the city, and there is a direct connection to PDX by TriMet’s MAX light rail network, we instead opted to take a rideshare to our hotel near Pioneer Square. At this point I had been awake for over 24 hours straight, utterly exhausted, and all I wanted to do was get to bed as soon as possible. The rideshare set me back around $30 but ultimately got us there about 30 minutes quicker without having to walk a half mile from the nearest train stop. Later in the trip we did return to PDX via MAX, and I can confirm that the rail connection is very nice and quite conveniently located compared to the distant walk to the rideshare area.

Getting Around Portland

The regional transit operator for the greater Portland metropolitan area is TriMet, named so because it operates in the three counties that make up the metro: Clackamas, Multnomah, and Washington. TriMet operates a pretty extensive network, including 85 bus lines, 5 light rail lines, and the WES Commuter Rail service. While not owned by TriMet, the agency also operates the city-owned Portland Streetcar system.

The crown jewel of the TriMet system is the MAX light rail lines, which run over nearly 60 mi (97km) of track on five different lines. The system is considered to be one of the best examples of modern light rail systems in the United States and helps contribute to Portland’s high transit ridership compared to other cities of similar size. As in other rail systems like Atlanta’s MARTA or Chicago’s L, interlining is used to increase perceived frequencies in the core sections of the system. Most notably, headways as little as 3 minutes exist in the city center during peak periods. The system operates primarily using Siemens rolling stock, with the oldest trainsets from Bombardier being phased out as more Type 6 trains are delivered. The oldest trains are pretty basic in terms of amenities and comforts, especially with some high-floor stepped trains operating on a low-floor system. New trains, however, offer more flexible seating arrangements, better lighting, LED destination signs, and fully level low floors for level boarding, providing for a more accessible transit experience.

Payment on all of TriMet’s services and on several other operators in the region like Vancouver, Washington’s C-Tran system is completed through Hop Fastpass contactless smart card system. All TriMet rides cost the same at a flat $2.80 fare for buses, MAX light rail, and WES commuter rail. While there are passes available for purchase, including daily and monthly passes, we did not purchase any during our visit. The ticket machines only dispensed tickets, no proper reloadable fare cards, and we were not sure how much we were going to use the network. Instead, we opted to use our contactless bank cards and mobile payments to tap in at MAX stations. This proved to be a fantastic way to get around, even if I enjoy a well-designed card as a souvenir. Hop also has a major benefit for riders both local and visiting in utilizing fare capping to prevent a rider from paying for more than the cost of a daily pass on their rides, or for the price of a monthly pass for that matter, as long as they use the same payment method.

During our time in Portland, the only TriMet service that we utilized was the MAX network, and even this was pretty sparing. Most of what we wanted to explore was either on foot or further afield than the (admittedly large) network could get us to. Onboard the trains themselves, we never ran into a problem, and the system seemed to be well utilized with a good amount of riders. There were, however, moments a couple of times at the stations where myself or one of my travel partners felt unsafe or uncomfortable. Though the situations were easy to resolve, it did leave a bad taste. Throughout my travels and experiences riding systems around the world, there have been very few times where I have been uncomfortable using a system, even on some that have a negative reputation like Boston’s MBTA and the Bay Area’s BART.

Despite this, however, TriMet as a whole is still the best way to get around the city, even with the slight problems I had during my time in Portland. The system is well used by locals, and there are great connections to popular sites around the city. The fact that the system is as large as it is, with as much use as it has, is marvelous for a city of this size in the United States. No system is perfect, and TriMet has its pinch points, but as a whole it is a great way for visitors to explore the Rose City.

Morning Rush

Waking up the next morning feeling like a person again, my travel crew and I decided the best way to start a day full of adventuring and lots of physical activity would be with a breakfast of low nutritional value. Before coming, we had spoken with another mutual friend who was a resident of the Pacific Northwest, and they gave us a small list of things we needed to see/try. On that list is one of the city's prime eating establishments, Voodoo Doughnut. We traversed the ten or so city blocks from our hotel to the flagship location, along the way getting a feel for the cityscape including popular sites such as Portland City Hall and Stumptown Coffee Roaster's flagship location before finally seeing the pink brick building adorned with neon.

After waiting briefly in the queue to enter the store (it's a small shop so there's often a line outside, even though it took us less than a five-minute wait), we were able to order our breakfast of champions. I decided on a chocolaty Boston Cream doughnut while my travel partners got a cookies and cream and guava. The doughnuts were, in a word, delectable, and we were going to need the calories in the day ahead. I’ve found that a lot of times the famous local restaurants can be hit or miss, but this place was a hit. Not only were the doughnuts great, but the entire storefront was very well done, along with the surrounding area being a pedestrianized plaza lined with other small shops and restaurants.

Finishing our doughnuts, our next stop was to visit a true Portland landmark, the White Stag sign. A staple of the Portland skyline and one of the most recognizable symbols of the city, the sign was installed on the White Stag Building in 1940 and faces the Willamette River, specifically where the Burnside Bridge crosses. Formerly advertising for different brands like White Satin Sugar and White Stag Sportswear, the sign was acquired by the city in 2010 and has read “Portland Oregon” ever since. No trip to the city is complete without walking along the Burnside Bridge to get a photo with the sign. The area surrounding the bridge has some unique offerings as well, such as the waterfront park which hosts a market on Saturdays, or the Skidmore Fountain.

We snapped some shots of the sign and then followed Burnside Street westbound up from the river. Along the way, we got to see more of the city environment, including passing by Chinatown’s gate and the North Park Blocks. Portland’s streets can vary drastically for a walk as short as ten blocks. One minute, you’re in a park or a well-shaded plaza, maybe walking along a boulevard with majestic trees rising from the median in the street. The next, it is pure concrete and asphalt to fry against.

Ten blocks up from the Willamette, we reached another must-see item of the trip for us, Powell’s Books. Powell’s flagship location is a sprawling utopia of books, often claimed as the largest independent bookstore in the world. I would believe the claim. The main building alone claims a full three floors of a large warehouse building, with a secondary building for technical books located nearby. As you enter the shop, you are greeted by massive wall-to-wall floor-to-ceiling bookshelves containing novels and collections of poetry from every corner of the globe.

One of my favorite parts of the store was the rare book room located on the top level. To enter, you need to obtain a room pass from the info desk next to the entrance and leave personal belongings like bags and water bottles on a shelf outside. Once inside the room, however, you get to see some truly one-of-a-kind items. When I was there, some of the offerings included a signed first edition printing of Douglas Adams’ Hitchhiker’s Guide to the Galaxy, a Dutch copy of Ptolemy’s Geography from the 1600s, and a second edition copy of the journals from the Lewis and Clark expedition, which included an original map. The journals were the most expensive item available in Powell’s, costing over $30,000. Making our purchases (which did not include the journals but did include a guidebook from Portland), we headed back into the bright sunlight and decided it was time to climb further up from the river to explore some of the more natural offerings available in Portland.

In The Garden

Weighed down with new books and the like, we were soon on our way westbound again, climbing higher through the city, stopping along the way to see Providence Park. The park is where Portland’s soccer teams (the Thorns of NWSL and Timbers of MLS) play, and is thought to be the oldest soccer-specific stadium used by an MLS team, first opening in 1893. We also made a stop for coffee at a staple of the Pacific Northwest, Dutch Bros. The opinion of the group seems to be overwhelmingly “it’s okay.”

After a little bit of searching and quite a bit of scratching in the sun until we reached the shadier residential streets in King’s Hill neighborhood, we reached Washington Park, the largest park in Portland and home to several of its famous outdoor attractions. Taking a quick breather at the Lewis and Clark Memorial Column, we paused to enjoy the view of downtown Portland below us, the buildings slowly falling below our sightline towards the river. Off in the distance we could see the snowcapped peak of Mount Hood.

Scattered throughout the park are miles of trails and dozens of statues, plaques, and public art. Along the way to the Rose Test Garden, we passed by the Sacajawea Monument and the Oregon Holocaust Memorial. One nice thing about Washington Park is how separated it keeps pedestrians and motor traffic. There were very few crossings and places we ran into vehicles (until we accidentally hiked along a road the wrong way for 20 minutes before realizing and turning around). The layout of the park is rather confusing, and the trails we were following would suddenly take a turn in an unexpected direction. Thankfully, after a while and consulting our phones’ maps, we reached the International Rose Test Garden.

Portland’s heavy clay soils and marine climate are perfect for growing roses, and the city has done so with gusto since the 1800s. The International Rose Test Garden cemented Portland’s reputation as the Rose City when it opened in 1917 to house varieties of the plants from war in Europe. Today it features more than 7,000 plants of hundreds of varieties in the oldest continuously operated public rose garden in the United States. Walking amongst all of the rows of blooming flowers, it is quite an impressive sight to behold. I did not know there could be roses of such shapes, sizes, and colors, filling the air with their rich and royal scents. Located across from the Rose Garden is the Portland Japanese Garden, widely regarded as one of the best Japanese gardens in the United States. We did not, however, visit; there was an entrance fee for the Japanese Garden unlike the Rose Garden.

Completing our stroll through the flowers, we were craving something a little less well-kept by man, and decided to follow one of the park’s trails. The lush Pacific Northwest forest canopy was welcome relief from the hot sun, and the hilly landscape cloaked in ferns and moss was an enjoyable shift from the midwestern farmlands we came from. There are miles of trails to explore throughout the combined 410 acres of Washington Park and the adjacent Hoyt Arboretum. Occasionally, the trees will clear, and you are met with a view of Mount Hood again or perhaps catch sight of the Japanese garden’s pools below, but other than that, the park feels very well disconnected from the rest of the city or even the outside world; it is a refuge of nature in the middle of the hustle and bustle of modern living.

We hiked for a few miles before reemerging from the forest near the Oregon Zoo, ready to catch a train from the Washington Park station on MAX. Washington Park itself describes the parking situation as “paid and extremely limited”, two things I prefer not to deal with whenever possible, so I was glad to have such easy access to a wonderful city amenity via public transit. The Washington Park station MAX is not only the only completely underground station on the network, but also the deepest transit station in North America at 260 feet below the surface. The station is so deep that there are not stairs or escalators to reach the platform level during normal operation, rather elevators which include a diagram showing just how deep the station is. At platform level there are other displays available too, such as a core sample from the drilling of the Tunnel and etchings showing some archeology of the local area. After a brief wait, our train arrived, taking us eastbound from the park to our next adventure.

Gorge-ous

Another “must see item” we were told about for this trip was Multnomah Falls. The falls were described as being one of the most beautiful sites in the Pacific Northwest, and we were eager to see it, but we did not have a car on this day of the trip. Thankfully, there was an easy way for us to get to the falls without much hassle. Columbia Area Transit (known as CAT and featuring a fine feline in their font) runs the Columbia Gorge Express, an express bus between Portland’s Gateway Transit Center and the city of Hood River, and one of the few stops along the way is at the entrance to the park. This was especially helpful for us as Multnomah Falls had timed entry during our visit, something we did not know before flying to Oregon, but was avoided thanks to the lack of restrictions if you rode the bus.

Even from the parking lot entrance, we could tell that the falls were amazing. Multnomah Falls spans two tiers and is the tallest waterfall in Oregon. The site first gained popularity as a stop on the Oregon Railways between Portland and Pasco starting in 1884, with the trail and bridge constructed in 1915, followed by the lodge in 1925. Although passenger rail no longer serves the falls, the train tracks are still there, and you can occasionally catch a Union Pacific rolling by.

We took MAX’s blue line all the way from Washington Park to Gateway station and paid the $10 fare for the Columbia Gorge Express. The bus was a pretty standard minibus, and service frequency is very limited, running only every two-and-a-half hours for most of the day. This ended up working well for us as we were able to explore a beautiful natural marvel without having to drive there. The drive itself was also incredibly scenic as the route traverses I-84 along the banks of the Columbia River, offering great views of the river gorge. About an hour and a half after leaving Washington Park, we arrived at the entrance to the park, and immediately we could tell why this was recommended.

Past the bridge is a relatively short but quite steep trail to the top of the falls. The roundtrip is approximately 2.25mi or 3.6km and takes about an hour and a half. The distance is short, but the trail is quite steep with a climb of over 800 feet (240m) in just over a mile. Along the way are 11 switchbacks, and you feel the elevation change at the various signs. While it is not a particularly strenuous or technical trail despite the elevation, those looking to hike the falls should come prepared with proper footwear, comfortable attire, and water. Additionally, maybe skip this hike if you are afraid of heights as there are many sections of the trail that have steep cliffs off the side without any railing, or if you have mobility concerns as the trail is unpaved. Despite these warnings, the views available along the river gorge are unmatched; the expanse of the Columbia River is an amazing sight to behold. Finally reaching the top of the trail, we were met with a lush and tranquil creekside with some smaller falls and rapids to relax by after our hike up. There is also a viewing platform to see the falls plunging over 540 feet (165m) down its main drop.

After a hike back to the base of the falls filled with more stunning views, and the compulsory stop at the gift shop for stickers and postcards, we made our way back to the bus stop. In total, we had nearly two and a half hours at the falls between busses, and this amount of time felt perfect for the quick run up and down the falls. It is possible to spend less time at the falls, especially if you do not continue up the trail past the first viewing area, or more time if you want to explore more fo the trails that branch off the main path into the surrounding Benson State Park. Part of the reason we did not stay and explore more of the area surrounding the falls, despite loving the immense natural beauty, was that this bus was the last of the day back to Portland at 6:50 p.m., and trying to get an Uber home would be next to impossible. Not to mention by this point in the day, we were exhausted, having walked nearly 10 miles (16km) including over some pretty steep terrain on a rather hot day. We decided the best course of action would be to get dinner, make our way back to the hotel, and regroup to prepare for the following day.

The bus ride back to Portland was just as scenic as the ride out to the falls, if not more so thanks to the quickly lowering sun starting to cast more of the gorge in shadows and paler shades. After a quick MAX ride from Gateway to Skidmore Fountain station, we found ourselves at Pine Street Market, a food hall with a variety of offerings. Based on our ravenous hunger and strenuous day, a rather hearty portion of ramen seemed in order along with some ciders. It was delectable, with the noodles being the right amount of chewy and the chashu pork. For dessert, we picked up some moon cakes from another stall in the food hall as a perfect top-off for the day.

Walking back to the hotel after dinner, we did decide there was one more thing we wanted to see to close out the day: the rooftop bar. The place was absolutely packed, but we didn’t mind since we were too tired for drinks anyway. Getting some nice views of the city and Mount Hood in the setting summer sun, we were content enough to hang out for a little while by the windows and railings, snapping a few photos. Finally, we decided it was time to call it a day and make our way back to the room.

Rather unusually for my normal trips, this trip was shared with a couple of friends and two full days in Oregon. Coming into the trip without many plans, we decided to spend the first day exploring more of the Portland-area proper and decided what to do for the second day once we were out there. After our experiences hiking the falls and enjoying more of the natural sites throughout the day, we decided the best way for us to spend the second day would be to rent a car (a first for me) and drive to the Oregon Coastline. Without much pre-planning, we were only running with a few basic ideas from what we were told by our friend and what we read in my new guidebook: Astoria as the site of the United States’ first city on the Pacific coast, Cannon Beach for Haystack Rock, and Tillamook for the creamery. Content with our rough plan and a newly made rental car reservation, we settled in for the evening, utterly exhausted but excited for what we would see the following day.