Portland is a weird place, and I couldn’t believe how truly different it was to any other place I had been. I spent a month investigating this beautifully colored, strange place - here is what it’s really like to live in Portland, Oregon. 

All the Recs, Comments & Videos at the End

After three weeks in beautiful mountain-side town of Bend, one of the happiest cities in the country, I was ready for my first real stop on this full time travel journey: Portland, Oregon. I’ve been told it’s a place where “there are a lot of people like you.” As a novice traveler, I felt a mix of excitement and apprehension as I ventured into the Silicon Forest. Driving through the streets of the Hawthorne neighborhood, my home for the next month, it became quickly apparent that these narrow streets were not designed for my black four-wheel-drive truck and it’s 30 inch tires. Driving was terrifying, but the location was a gem - only a 15 minute bike ride from downtown, across the beautiful Willamette River, a vein of life to the city and source of industry that built this town centuries ago.

After I secured a parking park within eyeshot of my airbnb I would avoid driving at all costs. Which was incredibly easy thanks to the vast bike-share program, sponsored by Nike. Hybrid electric bright orange bikes on most major street corners, waiting to accommodate your travel throughout the city. Nike app downloaded, AirPods as my navigation, I was ready to explore. Portland is likely the best city in America for cyclist and pedestrians. Ample bike lanes, and pedestrian first culture, Portland is designed to be able to get around without a car. As I pedaled through the city, wind in my hair, gripping the handle bars tightly with scared excitement, I was transported back to my childhood, when riding a bike meant freedom and adventure. A feeling I would relive daily, noting as a feature of what I wanted in whichever city I ended up.

Portland pulses with creativity and innovation. It seemed like everywhere I looked people were creating something - art, comedy, writing, food carts. There is a buzz of creativity in the air that is inspiring and infectious. My days often started with a short walk to a coffee shop to write, read, or work on content. Unique coffee shops with vibrant personalities were always within a ten-minute walk, a haven for someone constantly working side projects.

I’ve never thought of Portland as much of a sports town, but my first weekend there proved otherwise. Outside the Portland Trailblazer’s Moda Center Arena, a kind stranger who liked my Seahawks hoodie offered me a lower section ticket at a nose-bleed price. A season ticket holder whose sister couldn’t make it that Thursday. I repaid his kindness with an IPA at the end of the first quarter. An ex-basketball player himself, although it wasn’t clear if that was high-school or college, he’d tell me stories of him playing beside now retired pros. I’d pretend to know who he was talking about, and we’ both be in awe of how Steph Curry, from the visiting Warriors, could move with a basketball. Near the end of the game a random fan told me about a Timbers Football (soccer for the uninitiated) match on Saturday and where to sit for “the madness” of the fan section.

I take hints from the Universe, and after riding a bike to Providence Park Stadium on a beautiful spring day, I found myself at what I can only describe as the most fun I’ve ever had at a sporting event. IPAs in hands, chanting in full force, brilliant flags, noise makers and green smoke machines created an environment of pure absurdity and fun. To say they take their soccer seriously is a gross understatement. Wear something green, buy a ticket in the GA section, and don’t expect to leave with much of a voice.

Post-game, I met one of my favorite humans for drinks downtown. A Portlander herself, the choices she offered were nearly endless - breweries, wine bars, hip whiskey bars, to name a few. The options for food and drink spots are incredible in Portland, all with vividly unique personalities. A nice break from the corporate sameness you find in most cities. The Pope House Bourbon Bar appeared to be a Victorian style home dressed up as a bar with wraparound decks and Kentucky Derby feel. Cocktails were great, the black-eyed pea toast was a delicious snack; especially if you’re looking for less animal parts on your plate. A few blocks over, down a thin alleyway lined with hedges you will unexpectedly find an incredibly hip, quasi-hidden, European-style wine bar. The Serbian Orange wine was a winner - just one example from Portland’s eclectic food & drink scene that would continue to impress as the trip went on.

Good drinks and great company make for rough mornings, but I didn’t know how many sunny days were in store, so when the phone showed sunny and 70s I had no choice but to get out on the water. Kayaking on the beautiful Willamette River, with a unique mix of cityscape and greenery was an incredible experience that is right there in the heart of the city. On the southwest side of the river, near Willamette Park, you can rent your vessel at the Portland Kayak Company and launch right from the park. The juxtaposition of city vibes and natural beauty really is unmatched. Strolling through Portlands diverse neighborhoods you’re greeted by a kaleidoscope of flowers, an eclectic mix of home styles and store fronts with great personality. Look beyond to the hills in any direction and you’ll find lush green rainforest. Then there are truly epic places just an hour’s drive, like the Columbia Gorge. Greeted first by the awesome Columbia River, a force of nature that really can’t be contained with words. You really should try and get out for a hike like Eagle Creek Trail with too many waterfalls to recall. If you can muster the 12 mile, out-and-back hike, to Tunnel Falls it is an experience you will retell often back home. Hood River is an adorable river-side town, and great spot for a well deserved beer and lunch (Mussels at pFriem Brewery were off the charts). And make sure to fit a few wineries and orchards for picking fruit to round out a nearly perfect day. 

I’ve never been the most outgoing guy, but I was determined to get outside my comfort zone. It would be essential for understanding the people. While I wouldn’t say the people were the friendliest I’d ever been around, most people in Portland were legitimately interested in talking to strangers around them. I had several interesting conversations with a ton of different people. What I believe was a trans  throuple at the Space Room Lounge in Hawthorne was one of the first people I’d met. We couldn’t have been more obviously different but that didn’t matter. A theme that would continue to be on display in Portland’s culture. At a “secret” (IE hard to find) patio bar I had a wonderful conversation with a woman clearly too hip and pretty for me. Impressed by the two-tiered coloration of my New York Sour drink order we celebrated the joys of coaching soccer and the true terror of driving a pickup truck anywhere within city limits. I could go on about the guy with a great beard and soft demeanor outside of Common Grounds Coffeehouse who told me the entire life story of the stray Chihuahua that joined us for our morning coffee. Or the girl, waiting to meet a tinder date, who was reading the same book, “Wild”, as I. Portland just seemed to be set up for spontaneous interactions with interesting and random people. An element of culture I haven’t found in many places. Quite different than my hometown of Vegas.

I don’t know how else to say this, except that it just felt like the aggression levels were turned down in Portland. Maybe it’s the marijuana in the air, I don’t know, but even the unsheltered community seems more chill and non-threatening, especially compared to other cities. Yes, there's a new term for homelessness here, and if that turns you upside-down, this might not be the place for you. Portland is a strong advocate for the LGBT community, and people embrace being different here. You'll likely see more trans individuals than ever before, unless you're from Seattle. If that makes you uncomfortable, Portland may not be for you, and you should probably talk to somebody about those feelings. Like avocado toast — my palette is different, but as long as you’re not harming others, live your truth. Be different, do what feels right. And be careful with those knives, "Avocado Hand" is a real issue affecting thousands of millennials every year.

Downside? Things are expensive, and not just housing. Taxes, groceries, restaurants, transportation, almost everything except of a decent beer. It was unanimously always $7 for a good quality local IPA. The Spring April month brought fantastic weather my way, but I’m sure people would say the lack of sunshine, short days and rain in the winter can weigh pretty heavy on your mood. Others had mentioned that the lack of diversity. And while the food choices are culturally vast, the population is statistically 12 percentage points more white than the national average.

I loved Portland. The city is perfect for walking and biking, with unique food options at every turn. It's refreshing how you have to go out of your way to find a chain restaurant like Chipotle or Chili's. There's always something to do, any day of the week - stand-up comedy, live music, sporting events, poetry readings, and even Museum After Dark parties (yes, it's a real thing, and it's amazing). I had fascinating conversations with strangers and felt safe everywhere I went. For a nature fix, the Willamette River and beautiful city parks like Washington Park and Forest Park were perfect escapes. The creative energy in the air felt uniquely special. After 30 years in a desert devoid of community and culture, my expectations were low, but if Portland became my next home, I'd consider myself very lucky.

Huge THANK YOU to @gia.and.cats who gave me most of the recommendations & made this trip truly special by just being her.

Did I get it right? What’s your honest take on Portland?
If you got this far don’t be lame. Leave a comment below >

Recommendations from Friends & Strangers

• To Do:
  • TravelPortland.com is a great resource of things to do!
  • Timbers Soccer – sit in the GA (fan) section for most fun
  • BIKETOWN Portland App – Nike’s semi-electric bike share program to get around
  • Portland Kayak Company – Kayak rentals right on Willamette
  • Eagle Creek Trail (hike) – Beautiful hike in the Columbia Gorge up to or as little of the 21mi. you’d like with Tunnel Falls @ 6mi. in
  • Hood River – Great little town in the Gorge right along the River
    • pFriem Brewery for great beer & mussels
  • Fruit Loop – many wineries and fruit picking farms in the Gorge
    • Wy East Vineyards had Alpacas & a great Rose
    • Steve & Stone was beautifully placed with a great Pinot Noir Blanc
  • Tilikum Bridge of the People – No cars | river & city views
  • Powell’s Books – coolest used bookstore in the world
  • OMSI After Dark – 21+ evening museum experience | Garden Party theme was freakin awesome
  • Portland Night Market – monthly display of local small businesses slash food cart row slash petting zoo | very cool
  • Forest Park – over 80 miles of great hiking trails in the city
  • Hoyt Arboretum – living museum of trees in Washington Park
  • Kayaking: Willamette River (in city), Scappoose Bay (40min), Columbia River Gorge (40min)
• To Eat & Drink:
  • [Downtown] Atlas Pizza – by the slice | 36 Chambers Pizza is $$
  • [Multiple] Blue Star Donuts – Blueberry Bourbon Basil for the win
  • [Hawthorne] Apizza Scholls – Pizza place | amazing Calzone
  • [Hawthorne] Hinterland Bar & Food Carts – great outside area
  • [Hawthorne] Someday – very cool vibe cocktail bar (New York Sour)
  • [Hawthorne] Khao Thai – outstanding, and well priced, Thai food
  • [Hawthorne] Common Ground Coffeehouse – weird, fun vibes | open late
  • [Hawthorne] Albina Press – nice coffee shop, with outdoor seating
  • [Downtown] The Pope House Bourbon Bar – adorably themed, excellent small plates, & great cocktails
  • [Downtown] Bar Diane – Wine bar with European vibes | Orange Wine – Serbian 2020 Maurer ‘Crazy Lud’

Comment your recs below >