A weekend in Portland is like coming across that place in your dreams that you can never quite recall. Down every block there are striking familiarities: sights, sounds, and scents that you just can’t put your finger on. Or you can, but they’re not exact; they’re just little scattered pieces of other cities and towns you’ve been before. Or maybe that was just my weekend in Portland, and you think I’m talking crazy. Either way, you can expect that two and a half days in this city will be a whirlwind of excitement accompanied by deep breaths of pure, crisp air. When I look back on it, it somehow feels as if I did nothing while doing everything at once. And isn’t that the best kind of vacation? Not having to raise a finger, but getting the enjoyment and rejuvenation you’ve been craving? This particular playlist, filled with both the familiar and unfamiliar, was created to do just that. So wander over to your nearest hipster coffee shop, crank up the volume on your headphones, and read on for a little bit of Portland flavor and inspiration. You never know when you might need a weekend away.
Adventures in Downtown Portland
The infamous Oregon rain faded in and out throughout the weekend, but of course it was at its peak when we first landed at PDX. Since I’d only gotten a few hours of rest the night before, I started to worry that this seemingly sleepy, dreary town would be hard pressed to wake me from my grumpy stupor. After taking the train to a cozy breakfast nook downtown though, my spirits were in much better shape (not an uncommon result once good food is placed in front of me).
Anna Bannanas is your quintessential Portland cafe. Besides the two or three actual tables with chairs, everything else is just a random sofa, love seat, or arm chair by a fireplace. It looks a bit like you’ve just walked into your zany aunt’s house, and she’s inviting you to perch “anywhere” while she boils some tea. The paintings on the wall are crooked, almost purposely so. The rug is worn in, but homey. After ordering a pot of tea along with some scrambled eggs on delicious bagels, we sat curled up by the window, watching the rain pitter patter against the glass and fall upon the canopy of trees that lined the street.
Featured Song: Dream a Little Dream of Me by Cass Elliot
This may be a given for Portland, solely based on the peaceful sound of rain and thunderstorms before the song even begins. But this 1968 Mama Cass favorite is also one of the most atmospheric songs of all time. It’s got a great swing to it and an old-timey vibe, with a fuzzy spoken introduction, and it concludes with a round of lullaby-like whistling. Surprisingly, it’s not the original — In fact, a zillion other musicians did it first, dating back to its creation in 1931. This rendition has so much unique personality and charm to it though, you wouldn’t have a clue. “Sweet dreams till sunbeams find you, sweet dreams that leave all worries behind you.”
Our check-in at deLuxe wasn’t until 4 (seriously…what a wretched rule among hotels), but we decided to crawl to the front desk at 11 am in hopes that our tired worn out faces would be taken pity on. I’d reserved the hotel partially based on price, location and good reviews, but I was also intrigued by its Old Hollywood theme (despite having just left Hollywood). When we arrived, the large glass doors were opened for us by the doorman, and we were met by a glamorous carpeted staircase that ascended towards a chandelier, and to my surprise and glee, a gigantic lit-up photo of Jimmy Stewart in my favorite Alfred Hitchcock movie, Rope.
We headed towards the gold-accented reception desk, feeling slightly out of place in our grungy airplane attire and backpacks…but come on, this is Portland, right? Luckily, the woman who greeted us was lovely and made us feel right at home when we asked if an early check-in was possible. Much to our relief, it was.
Our room was small yet elegant, with little classic touches throughout, like the black-and-white photo of Ginger Rogers that hung on the wall by the door. The King-sized bed took up most of the space, and it’s crisp white sheets beckoned to us; especially knowing that they weren’t tainted with cat litter particles like the ones in my apartment constantly are (a true vacation indeed). We drew the curtains closed and threw ourselves onto the bed for an epic nap before the rest of our adventure ensued.
When we awoke feeling refreshed, we decided to hit the town for a late lunch. About a mile away from our hotel was the famous Elephant’s Delicatessen. I’m not generally a fan of tomato soup, but my boyfriend who grew up in Portland, insisted that I had to try it. The rain had cleared out during our nap and left a bluish grey fog above the city, so we decided to walk and enjoy the crisp air that is so rare in southern California. The wet cobblestone and lush greenery aligning the streets and apartment stoops actually reminded me of my old neighborhood back in Brooklyn, which provided an odd comfort.
Elephant’s was even better than I had been led to believe. The cheese and wine selection was overwhelming yet approachable. Everyone who worked there was equally as Portland hip as they were Portland friendly. And the tomato soup!…It was truly one of the most delicious things I’ve ever eaten, and made me rethink my dislike for it to begin with. Let me stop raving for a second though, to interject that this really is no ordinary tomato soup. The magic ingredient is a hefty dose of orange juice, along with some pretty large portions of onion, cream and butter. When you stop in to grab some (which you inevitably will after that description), make sure to get a bread roll or two for dipping – It’s otherworldly.
After we’d stuffed ourselves with more soup and bread than we should have, we decided to top it off with the obvious next choice: beer. Blue Moon is a cozy neighborhood pub just down the street, and it’s owned by McMenamins: a local company that runs an eclectic mix of breweries, bars, concert venues, and even historic hotels throughout the Pacific Northwest. The local favorite in Portland is the bohemian-style Crystal Hotel and Ballroom, which I plan on prioritizing in my next trip.
As for Blue Moon though, it’s one of the most comfortable, homey and well-decorated bars I’ve ever set foot in. The bartenders are just as friendly and down to earth as you might imagine, and the old-fashioned fireplace crackles happily as you order your drinks. While I’m actually not much of a beer drinker, I was impressed with the flight we ordered; especially the Grapefruit ale. Take that recommendation with a grain of salt of course, because you can be pretty sure I’ll always choose the fruit beer as my favorite.
Fast forward two hours later and we were finishing up a heated third game of Shuffleboard, not realizing that so much time had past since we’d first walked in. As I haven’t been all that entertained by bars over the past couple of years (late twenties, be damned), my average outing these days probably lasts a whole 45 minutes at best. Suffice it to say, Blue Moon won me over. As our cheery bartender slid our check across the copper-plated bar, I decided I’d definitely be a regular if I were ever to ditch LA for Portland in the future.
Featured Song: Addicted to Love by Florence + The Machine
Continuing down our path of power-house female vocalists, here’s another great cover that I heard for the first time just recently. The original by Robert Palmer is a load of fun, and I’m always jazzed when it plays on the oldie station (which is all the time), but this 2011 slow-building Florence Welch execution is top knotch. There’s some heart-wrenching echoey harmonies going on throughout, and the drums kick in at just the right moment. “You like to think that you’re immune to the stuff, it’s closer to the truth to say you can’t get enough.“
An impromptu evening in Northeast
Around 9 that very same night, we were whisked across the Broadway bridge in an Uber, while glittering city lights whirled by on our way to the Northeast side (or as Portlanders refer to it, simply “Northeast.”) If you had asked us what our plans were an hour earlier, we’d have told you that we didn’t have many, other than consuming wine and cheese in hotel bathrobes like a couple of pretentious pricks. But then I decided to hop online and glance at Time Out, just to see what was happening in town that evening, and I came across a familiar name: Agnes Obel.
If you haven’t heard of her yet, She’s a truly bad-ass songwriter from Berlin with an incredible voice and a plethora of musical abilities on various instruments. The funny thing is that I’d only recently discovered her music while randomly listening to NPR one night, but had been immediately entranced and was soon raving about her to everyone. You can now imagine my surprise when she just so happened to be playing a $6 show in Portland on the one evening I was in town. And Voila!…That’s how we ended up without wine, cheese or our bathrobes, standing wide-eyed in front of Wonder Ballroom a mere 30 minutes later.
The dimly lit, woodsy bar beneath the ballroom was the perfect place to grab a cocktail before the show. It was beautiful while slightly eerie, and you could always catch a glimpse of what was happening upstairs, since there was a screen with a view of the stage set up on the wall. Once Agnes and her band appeared, we ran upstairs and joined the crowd to watch her set begin. For the next hour, the audience was dead silent, standing almost completely still, practically haunted by the beauty of the music echoing throughout the space. There were four women in total; one on violin, one on cello, one on percussion, and finally Agnes, accompanying herself on keyboard. She spoke timidly a few times throughout the show, telling off-the-cuff stories in an exotic accent about what inspired various songs she’d written. And as you may have guessed, by the time we left that evening, Michael and I were both gushing about the huge crush we’d just developed on Agnes Obel.
Featured Song: Familiar by Agnes Obel
What in the world is this magical masterpiece? When I heard it for the first time driving home from work late one night, I instinctively started grinning from ear to ear like a lunatic. All the voices you hear, all the endless layers of cello and violin; it’s all recorded, produced and mixed by Agnes. Watching her show at Wonder Ballroom was like a strange wonderful dream, and it took me straight back to the thrill I got during that very first moment in my car. This is what music is supposed to do to you — when it’s good.
“We took a walk to the summit at night you and I, to burn a hole in the old grip of the familiar. And the dark was opening wide, do or die, under a mask of a million ruling eyes.”
A Day in Sunnyside
On our second and final full day in Portland (I’m a speedy adventurer but a long-winded writer), we headed over to the Southeast side of the city to spend the day with my sister. Because of the nonstop rain we’d encountered the day before, I was expecting to have to finally give in and buy an umbrella. But my sister’s neighborhood stayed true to its name (boasting that it really was the sunny side), and we were able to enjoy the fresh spring air sans umbrellas or jackets. Sunlit spring petals in rosy pink canopied the trees and sidewalks on the blocks leading up to Tera’s house. I was especially struck by the eclectic variety of victorian homes and funky bungalows that we passed on our way, each of them showcasing wild shades of purple, green, or blue.
About an hour after we’d first arrived on her stoop, we shuffled back outside with a much larger party: Tera, my nephew Elliot and their two fluffy dogs: Cookie and Otis. After walking just up the street to take a look at Elliot’s quaint little middle school and all the chickens that were being tended to there (nothing more Portland-y than that), we headed a few more blocks north towards Laurelhurst Park. There amidst the sprawling meadows, the weeping trees and the budding flowers, my Brooklyn nostalgia really took hold. The setting felt so similar to my old stomping grounds in Prospect Park, which was always my favorite place to spend a sunny Saturday afternoon lying lazily on a blanket in the grass. While we couldn’t do much lying around here with two high-energy dogs and an 11-year old boy in tow, we did take a picturesque walk around a glimmering lake and through a forest of towering trees. When hunger struck, we decided it was time to trot off to the main strip in Sunnyside for some lunch and shopping.
Hawthorne Boulevard is the ideal neighborhood street, bustling with quirky coffee shops, vintage boutiques, and of course, an abundance of thrift stores. We immediately found a cozy cafe called The Hazel Room that was just to our liking. The rustic, homey atmosphere welcomed us, as did the gigantic menu, filled with a diverse array of brunch items, soups, sandwiches and tea lattes. As a side note, we ended up coming back again the following afternoon to grab lunch and some surprisingly delicious cocktails before our flight – it was the only place we visited twice during our short weekend, which should speak for itself. Other Hawthorne points of interest included an artsy jewelry store called Altar where I found some great earrings (conveniently located right across from the cafe), and a funky hat shop that housed an amazing but stupid amount of fedoras, newsboy caps, and berets. As our Walking Tour of the Hipster Stores of Portland came to a close, we were finally tired out and ready to traipse back to the house.
Featured Song: Older and Taller by Regina Spektor
I’ve recently gotten into a few Regina Spektor songs, and this bouncy little tune is a gem off her latest album. It’s got that perfect melody I can listen to over and over again without getting tired of, since there’s plenty of variation within each verse. It’s also simple and raw enough to sound just as great live, with only her voice ringing out over the piano (along with some very coordinated clapping during rests). It’s a song that gives me the same easy delight that I got from a walk around Sunnyside; a reminder of life’s bittersweet charm.
“Enjoy your youth sounds like a threat, but I will anyway.”
The Trail Blazers at Moda Center
To finish off our whirlwind weekend, we spent the rest of the evening at the Trail Blazers game, surrounded by a sea of diehard Portlanders. While I’m the very last person you’d ever call a sports fan, I did enjoy the experience mostly due to the insane variety of food options. I started the night off with some great pizza, and later returned to the maze of local pop-ups for a tray of Nachos during halftime, which is how the following encounter occurred. As I was trying to juggle my food, drink, napkins and purse back up to my nosebleed seat, a very large, very drunk dude came beelining towards me. I silently prayed he didn’t have any idiotic plans to interact with me, but to my horror, he pointed a finger directly at my chest. I immediately tensed and got ready to brush him aside, when he mumbled something nonsensical at me. “What?!” I asked, confused. “You’ve got cheese on your chest, miss. Just wanted to let you know.” I looked down, though I didn’t need to, because I knew he was right. And there it was — A trail of nacho cheese dripping from the ends of my hair to about halfway down the middle of my shirt. I grimaced, laughed awkwardly, and then sort-of thanked him, since there’s nothing like a lesson in humility to conclude an almost picture-perfect weekend in the city of Portland.