As I celebrated the New Year in New York City, I had no idea I would be exposed to a completely different city on the opposite side of the country just three weeks later. I found myself in Portland, Oregon: a unique city that blends the active Pacific Northwestern lifestyle with interesting people, art, businesses, and forms of expression.

My day trip to Portland was part of a larger, 6-day/5-night trip to Seattle, Washington to visit a friend. We had discussed visiting Portland before the trip, but at the last minute, it appeared we might not travel to there. I was a little bummed, but I hadn’t done any research on the city, so I wouldn’t know what I was missing.

But as plans changed again, we decided to wake up early on a January Sunday morning and make a day trip to the City of Roses.

All pictures were taken by me unless otherwise credited

My Trip to Portland, Oregon: January 19, 2020

We would leave before 7 AM to make good time and enjoy our day in Portland. The ride was a straight shot down Interstate-5, a smooth ride once we exited Seattle. Without stopping, the 182 miles between Portland and Northern Seattle can be completed in about three and a half hours.



Before actually going to Portland, however, we had to stop at a must-see attraction nearby. Multnomah Falls features a breathtaking waterfall, split into two tiers. The natural recreation site attracts over two million visitors per year, making it the most visited nature site in the Pacific Northwest.

I had never heard of Multnomah Falls, not knowing too many places in the Northwest, but I couldn’t be happier that I got the chance to take in the views the site had to offer.

Located 30 miles east of Portland, I would highly recommend a stop at Multnomah Falls to anyone that finds themselves in Portland or Oregon, even if just for a day.

After parking in a decent-sized lot on Interstate 84 (apparently, different than the I-84 I knew in my hometown on the East Coast) there was a short path under the highway which allowed quick access to the falls. There was a coffee stand near the entrance, and we were definitely in need, grabbing a hot cup to nurse on our way up.


The first tier of the fall sees water fall 542 feet, creating a mist as the water reaches the ground. The second tier of the fall is just a 69-foot waterfall. In between the different levels is a pedestrian bridge, offering a great angle to take in the scope of the falls.

The trail from the bottom was well-traveled, with many other people taking in the waterfall on the clear Sunday morning. After the pedestrian bridge, the trail became less traveled but with good reason: it was slippery and narrow in parts. The snow and slush on the trail was leftover from a few days ago, so I couldn’t imagine traversing the trail in the midst of fresh snow or below freezing temperatures.

The path eventually would have led to the top of the waterfall and an undoubtedly cool view, but we decided not to brave the 11 switchbacks required to get to that elevation. The hike wasn’t for nothing though, as the views of the highway, Columbia River, and Washington state across the way were beautiful.


Multnomah Falls was an early highlight of the day, and a great example of the incredible Pacific Northwestern sights.

After we finished up at the falls, we headed back west, typing Downtown Portland into the map and locating a parking garage for the day.

With an appetite worked up, we decided our first stop would be food, at one of Portland’s many food truck locations. The food cart plaza I picked out actually took us across the river, over the Williamette River on the Hawthrone Bridge.


While the walk to these food carts was a bit out of the way, it was well worth the extra effort. The food cart plaza had seating and a few different options, though about half of them were closed on this quiet January Sunday. There was a Mexican food truck open that caught my eye, but we both decided on Tahir Square, an Egyptian/Middle Eastern cart.

Personally I’m a vegetarian, and I was excited to order the falafel supreme sandwich. It was almost definitely the best dish I ever had of its kind. The sandwich, more of a wrap, contained “Falafel, lettuce, tomato, tahini hummus, eggplant, fries cucumber, parsley and onions. Wrapped in toasted pita.” Just thinking about it makes me crave another taste.

My friend got a schwarma dish that she said was also delicious and worth the extra distance.

The walk from the parking garage, to Eastern Portland for the food cart, back to downtown Portland would help tack on to the amount of the ground we covered over the course of the day: but more on that later.

Specific goals for the day included checking out Portland’s flagship Nike Store, getting a treat from the famous Voodoo Doughnut, checking out some iconic Portland signs, and of course, sampling some of the Oregon city’s coffee. We would do all that and more in a jam-packed day.

In many ways, Portland was a lot like Seattle, three and a half hours to the north of it. The Pacific Northwestern cities shared similar vibes, while still each holding unique features and atmospheres.

Growing up in Hudson Valley, New York, about 90 minutes north of New York City, I grew up with certain expectations about how cities were. But compared to NYC, Portland (and Seattle) were totally different. Cleaner, way less traffic, less noise, less hyper-commercialization. The people were friendlier, and the mood in the air was just generally good.

This wasn’t just me trying to enjoy my vacation, as Portland was voted the 14th-friendliest city in America in 2016.

But what makes Portland unique is it’s “weird” vibe. In the same article, Portland was also listed as the third-“geekiest” city in the nation.

“Keep Portland Weird” is a mantra, a motto, and a mission, all rolled into one fun phrase. The slogan, originally intended to support local businesses, has gone on to include all forms of expression, including fashion, identity, art, and lifestyle choices.

There were definitely some interesting and unique people on the streets, art that blew New York City graffiti out of the water, and a slew of local businesses, with some being unique in their offerings or appearance.

Hip-Hop Connection: Visiting the city of course brought to mind “Portland,” by Drake featuring Travis Scott and Quavo. Travis Scott delivers the song’s name-sake in his verse. For rap news, reviews, and updates, follow B-Sak Rap Blog on Twitter!

A final observation about Portland would have to be the homeless population. Being accustomed to New York City, I didn’t think this issue would throw me off. While the volume isn’t even comparable (New York City has over 78,604 homeless individuals, Portland has around 14,000) the problem was still prevalent.

Perhaps, without millions of pedestrians, flashing neon signs, and taxis at every corner, the issue was more apparent. It was hard to walk far without seeing someone lying on the ground in blankets, pushing a shopping cart, or just basking in the sun with nothing else to do. It was very favorable and sunny January day, but I feared for how these people lived in colder and nastier conditions.

One huge difference from my East Coast experience was the allowance and appearance of tents. More so down by the river and under bridges, there were many pop-up camping tents set up, obviously sheltering some of the homeless. While this would be shut down in a heartbeat in New York City, Portland police have “no official policy on clearing out the camps or relocating homeless individuals” (per

On a more positive note, the people I saw that appeared to be affected by homelessness also seemed more well-kept than what I would expect, in both personal appearance and physical possessions, from clothes to even phones. For a city that experiences chronic homelessness, many of these people have adapted to the lifestyle in a city that is far more forgiving than East Coast counterparts.

Back to our sightseeing, we would make stops at the Nike Flagship Store, a book store, and Voodoo Doughnnut.

We didn’t stay long at the Nike store, but it was definitely cool and full of unique products. I thought the Russell Wilson display was cool, as well as the Michael Jordan statue suspended in the air. It was Sunday afternoon and the AFC Championship was on, with the Tennessee Titans holding an early lead over the Kansas City Chiefs.

The most active part of my website is Sak Sports Blog, so under normal circumstances I would have been all over the game. But between enjoying my West Coast vacation and the company on it, football was, for once, the last thing on my mind.

Voodoo Doughnut had a moderate-sized line out the door, a testament to its status as a must-stop location in Portland. The line moved quickly and once inside, we could see the menu and choose a doughnut to snack on. Having just eaten, I wasn’t in the mood for anything heavy. One of the doughnut’s caught my eye, and fit the bill as a cheap, lighter option. I couldn’t resist, as the doughnut called my name for… novelty reasons.

My friend went with the signature Voodoo Doughnut, and after she shared a bite, I realized I made a huge mistake. My “simple” doughnut paled in comparison, and after a nice hike (which we’ll get to in a minute,) I definitely would have had the appetite for one oe even two of them.

Image result for voodoo doughnut
The Voodoo Doughnut was covered in frosting, had some kind of jelly-filling inside, and was all-around an amazing doughnut. I dropped the ball going for a funny one instead. (Photo: The Ear Collector)

We also explored Powell’s City of Books, a massive bookstore that claims to be the largest independent new and used bookstore in the world. The sprawling bookcases were separated in rooms defined by color. We split up and explored our own interests in the store, and I quickly found myself getting lost even with directions hanging from the walls. I didn’t make any purchases (my friend did) but it was still a cool experience and definitely a place to check out if you’re ever in Portland.

After the bookstore we were ready for our second round of coffee on the day and our first in Portland. We would do so at Stumptown Coffee Roasters, a signature Portland franchise.

I was intrigued into where Portland’s “stumptown” nickname came from. Apparently, during the cities rapid growth in the mid-1800’s, rapid land clearing left many tree stumps behind in their wake. A couple months after my trip to Portland, my mom was watching Stumptown, an ABC television series. I quickly deduced the show took place in Portland, a neat thing I never would have guessed if not for my personal exposure.

After having like a dozen of cups of hot coffee on my trip so far, I decided to order a cold brew coffee at Stumptown. It was great, and kept me energized for the long day.

As promised, we also had to travel to and snap pictures of iconic Portland signs along the way.

The “Keep Portland Weird” mural was right near Voodoo Doughnut, while the Old Town sign was a just a short detour away.

So before 2 PM, we accomplished our goals of:

  • Visting Multnomah Falls
  • Getting a Voodoo Doughnut
  • Taking pictures of both Portland signs
  • Getting local coffee
  • Visiting the Nike Store
  • Eating from a local food cart

With plenty of time left to kill, we explored our options. A couple that caught our eye, but didn’t seem like home runs, were a Japanese botanical garden and a historical mansion. While they wouldn’t even be open due to time or season, they would end up guiding us to the activity that would fill the rest of our visit and provide some amazing sights of Portland.

We set out for Pittock Mansion: again, not to visit the mansion, but for the hike and the views of Portland it would offer along the way.

Along the way, we stopped to check out the exterior of Providence Park, an outdoor sports stadium best known for being the home Major League Soccer’s Portland Timbers. We were both Sports Management majors in school, and had worked in the world of soccer, so we definitely had to take a look.

Some fun facts about the stadium, since I’m really into sports venues:

Providence Park

  • Opened: October 9, 1926
  • Renovated: 1956, 1982, 2001, 2011, 2017, 2018-2019
  • Capacity: 25,218 as of 2019
  • Surface: FieldTurf
  • Current Tenants: Portland Timbers (MLS,) Portland Thorns FC (NWSL)

Soon after passing Providence Park, the roads would start to incline and our hike would begin somewhat unceremoniously as we were at the base of Portland’s West Hills. One moment, we’re walking on a road, passing stores in Portland, and the next, we’re surrounded by tall trees and nature. It was a little surreal, in the best way possible.

The main goal was to hike high enough to get a sweet view of the city. We didn’t know exactly how far or long that would take us, but set out on the beautiful, secluded trails. While there were some peeks at the city early in the hike, they were nothing compared to what we would eventually find at the top.

The trails were contained within the larger area of Washington Park. Again, the foliage and scenery, not even a mile removed from society, was absolutely breathtaking. Trees towered over us in all directions, as we took the Wildwood Trail for the majority of the hike. Wildwood is also the name of my favorite vacation spot in New Jersey, so I thought that was cool.

The striking sights reminded me of a movie: Star Wars Episode VI: Return of the Jedi. Scenes on the Ewok planet of Endor were filmed in the Redwood Forests of Northern California. The West Hills in Portland are about 450 miles north of those forests, and the trees here weren’t redwood. But it was still the closest thing I would see, as forests and trees just don’t look like this on the East Coast.

Besides the creatures and stormtroopers, director Howard Kazanjian created a fantasy world that believably seemed like a distant planet: using a natural place on our Planet Earth. What other sights are out there that seem too surreal to be actually happening on our planet? It’s one of the many thrills of traveling and seeing the world, expanding one’s horizons and view of the Earth.

Image result for return of the jedi ewok forest
Photo: Star Wars Episode VI: Return of the Jedi (1983)

The hike never forced us to go directly vertical, but it was definitely a good workout. The Wildwood Trail made twists and turns, bringing us both up and down as we progressed towards Pittock Mansion. I wasn’t really expecting to go on a dedicated hike that day, and I turned out to be under-dressed for the occasion. My jeans would become covered in dirt, along with my athletic shoes.

I hadn’t even packed any boots for my cross-country trip. My friend told me I definitely should have, as any day in the Pacific Northwest could potentially include a hike. Sure enough, we found ourselves out and about in nature nearly every day while I was there. Hiking boots will be an essential the next time I hit the West Coast.

A stop along the trail would humble me for the second time that day: the Oregon Holocaust Memorial.

(Photo: Google Maps)

On the left hand side of the memorial was historic exposition, explaining how Adolf Hitler and the Nazi Party rose to power, how they targeted and rounded up Jewish people and other populations, and how much of the world stood by idly during these horrific times.

Normally I’m a speed reader, but I found myself really slowing down, absorbing the information and taking the time to think about it. On the right hand side, much bigger, were first hand accounts, stories, and quotes from people imprisoned during the Holocaust. Each one was heartbreaking in its own way.

We would also pass by the Portland Japanese Garden and Washington Park Amphitheater on our way up. There wasn’t much to do at either of these locations, but the area was pretty nonetheless. Some of the city of Portland was clearly visible from here, but again, our ultimate viewing point would end up being so much sweeter.

After following the winding trail for a bit (I’m not even sure how long it took,) we finally reached our destination: Pittock Mansion, with an incredible view of the city and an enormous snow-capped mountain in the distance.

(I can’t believe this is an actual picture that I took myself)

While I think this picture is great, capturing the city, sky, and towering Mount Hood in the distance, it still doesn’t do justice to the beauty of seeing it in person. If you’re ever in Portland, the hike to this view is so worth the effort. If physical activity limits you, you can also drive/Uber to Pittock Mansion to take in this incredible sight. But if you have the ability to complete the hike, the payoff is that much sweeter.

Some fun facts about Mount Hood in the distance:

  • Mount Hood is a “potentially active” volcano, officially considered dormant
  • Elevation: 11,249 feet (highest point in Oregon, 13th-highest in US)
  • Prominence: 7,706 feet (28th-most prominent peak in US)
  • Hiking: Timberline Trail covers 40.7 miles with 7,300 feet of elevation gain


The viewing spot was crowded, but getting in a good position to take a picture wasn’t too difficult. We dug into our Voodoo Doughnuts, a well-earned treat after walking all day. Again, I found that I made the wrong decision, choosing a simple “novelty” doughnut over the signature Voodoo Doughnut.

From our lunch at Tahrir Square food cart earlier in the day to the Pittock Mansion vantage point, we covered at least 5.4 miles with over 1,000 feet of elevation gained. From Providence Park, the last major stop before the hike, to the top of the hills, we covered 3.2 miles with all 1,000 feet of elevation gain yet to be had.

This map shows a straight path from Tahrir Square to Pittock Mansion via the Wildwood Trail, but we covered even more ground with sightseeing along the way.

In just a day, we covered a good amount of ground in Portland. After trying local coffee, food, stopping at popular locations, and hiking to gain a birds-eye view of the city, it’s safe to say we made the most of our trip.

Checking the data from my phone, I covered 13.8 miles on January 19. Some of that came the night before and in the morning before departure, but at least 12 miles were covered in Oregon, a state I had never visited before. Between the brief hike at Multnomah Falls and the longer one on the West Hills of Portland, I also climbed 88 flights of stairs that day, easily the most of any day during the month of January.

Finally, using Swarm, which allows me to check-in to different locations I’ve been, I can see a map of the places I visited in Portland that day. Unfortunately, I forgot to make any check-ins in the final part of the day, leaving out Pittock Mansion, the Wildwood Trail, and the Holocaust Memorial. Still, the map below covers pretty much everywhere we stopped up to Providence Park.


With all that walking under our belt, along with dwindling daylight, we opted to take a Lyft from Pittock Mansion to the parking garage.


Coming into 2020, I had no plans to visit the West Coast, and certainly not Portland. It definitely seemed like an interesting city, but with so much of the world to see, I didn’t have it on my immediate bucket list. But after traveling to Seattle, the seven-hour round-trip drive to also see Portland made my first Pacific Northwest experience even better.

I decided to write about Portland before Seattle, seeing it as a smaller task to tackle. I only spent one day in Portland as opposed to five/six days in Seattle. But here I am, over 3000 words later, covering just a single day of my life.

Writing about my experience, and of course looking at the pictures, brought memories flooding back. I look forward to sharing more of my experiences on this website, as well as going out into the world and making new memories (as soon as the Coronavirus pandemic is over…)

Hopefully my story shows you that Portland has a little bit of something for everyone. Besides travel costs to get from Seattle to Portland, we had an activity-filled day at little to no cost, besides food.

If I ever went back to Portland, additional things I would like to try/see include:

  • Local restaurant
    • Food carts are an essential part of the Portland experience, but if I ever went back, I would be interested in trying a local, sit-down restaurant.
  • Japanese Botanical Garden
    • We did pass it, but the garden appeared to be out of season anyway. In full bloom, it sounds like a lovely place to take in the scenery.
  • Moda Center (formerly the Rose Garden)
    • It would have been a detour to visit the Moda Center, home of the NBA’s Portland Trailblazers. I didn’t really feel the need, but if I had another opportunity, I would walk around outside, and if there was a game, maybe even attend one at the former Rose Garden.
  • Coffee, coffee, coffee
    • I had coffee at Multnomah Falls (very good, exceeded expectations for a coffee stand) and Stumptown (a good Cold Brew coffee.) I had enough caffeine for the day (and after many cups in Seattle, enough for the week) but I would have loved to sample more local Portland coffee.
Moda Center - Rose Quarter
The Moda Center (formerly the Rose Garden) is home to Damian Lillard and the Portland Trailblazers. (Photo: Bruce Ely / Trail Blazers)

I had seen the opening episode to Fred Armisen’s Portlandia before, but besides that, and the “weird” mantra, I didn’t know much about the city. But after spending a day in Portland, I understood why it’s a popular city and place to visit. Re-watching the opening montage to Portlandia hit so different afterwards. I recognized the locations, the references, and felt connected: hey, I’ve been there!


If you liked this article, and want to talk about it, be sure to hit up Sakmann News, Entertainment, and Sports (aka on Twitter!

In the future I’d love to do more articles about traveling to different places. Naturally, my next step would be chronicling my adventures in Seattle that took place during the same week.

If you want to check out more from me, explore this website and it’s sub-sections. You can also follow these accounts on Twitter:

Thank you for reading: I hope you learned something, were inspired, or at least enjoyed your time reading about my trip.


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