Hilary Spencer Creative Photography » Creative photographer specializing in weddings, engagements, and family photography. I'd like to make you smile.

Portland Solo Trip – Part 2, Sunshine, Spektor, and the Kindness of Strangers

I tend to be that one that you’ll end up in deep conversation with. You know, the type that you’ve just met yet somehow you feel like you’ve known me for years. It’s my superpower. My flight to Portland left super early in the morning from Toronto and lead me to Minneapolis for a layover. That first flight was so fast I barely had a chance to nod off, but I was wide awake when I was the last of 5 people waiting to get on the flight without assigned seats. It’s nothing in comparison to getting taken off a flight – but they did ask for volunteers to move their flights to a later time, for a cash reward. Overbooking sucks, man!

I ended up on the flight sitting next to one of my fellow unassigned adventurers and ending up having some great conversation throughout the flight to Portland. He was headed to visit relatives, and offered a few recommendations for spots to hit up. While we didn’t get into super personal details territory, he did offer something that stayed with me the entire trip – it will be an opportunity for some clarity and reflection. I’m sure it was said in better words (if you’re reading this, I’ve butchered a great moment, I should have written this sooner!) but it stuck with me each step of my trip. I’m incredibly thankful for meaningful conversations in unexpected places.

We landed and I caught a glimpse of Ikea from my window. I swear, the most recognizable land mark in every city we visit. I went through the usual Airport paces and headed to pick up my rental car. It’s as if they knew I was a 20-something female travelling on her own; the guy pointed me over to my whip for the next week, a ridiculously cute white Ford Fiesta. I honestly squealed. How silly we are to put any value in the look of a vehicle, yet here I was – squealing over my tiny happy car. Thank you, Universe. I needed a cute ride.

Killed time before my AirBnB checkin at my sanctuary. My home away from home. My long lost Target. Why they had to take them away from us up here… it hurts to see such beautiful things yet can’t take them home! I had to avoid the home section in case I fell in love and had to leave anything behind. And yes, it was in Target that I purchased The Hat. The iconic new piece of me that gave me a bit of weird satisfaction starting off this trip.


The Tiny House. Oh, the Tiny House. It was absolutely perfect. I drove down streets that were perfect Portlandia, parking next to a tie-dye painted hippy van under a lush tree to the sounds of chickens and ducks. There sat my new home for the next week, impossibly small but absolutely perfect. I settled in, took in my bearings in the Scandinavian-esque home, climbed up into the loft bedroom and napped in the afternoon sun. This was excellent.


After a little stretch and *I can’t believe I’ve got the rest of the week ahead of me* wonderment, I had to get on with my day – I had a concert to go to! Regina Spektor was playing in town and I had purchased tickets the week before. I had wanted to keep this trip fairly open, schedule-wise, but booked in a few pillars of structure to keep things grounded. I hadn’t listened to Regina in years (oh the drives around Oshawa at 4 in the morning as a teenager, CD’s with playlists named after feelings and friends you couldn’t imagine your life without) but I did a bit of homework before I left. She is timeless. So incredibly, insanely talented and humble to boot.


I did a bit of a walk through downtown Portland (parked far too far away from the venue, which has a few different buildings under the same umbrella name in the city – way to go, Hilary – first night and you’re already screwing up!) and everything was blooming. I was told that the climate there is similar to Japan (you’ll hear about the Portland Japanese Garden later) in that it is incredibly wet, and they had gotten their Spring a few weeks before us Torontonians. Giant looming trees in the middle of a downtown core always gives me this feeling of nature prevailing over city sprawl.

It’s from here that the story gets interesting (if you’ve kept up with my monotonous play by play so far) – I get into the theatre, and find a lineup for drinks. I hadn’t technically eaten dinner and absolutely wanted a beverage to go with my experience. An attendant is checking ID’s and I chuckle as I hand him mine – “I’m from Canada! Date is down there.” He barely glanced at the ID and said “We can’t accept this, we’ll need your passport.” Shiny, happy, bubbly, *the world is my oyster* Hilary got knocked down a rung and I frowned. “Oh, ok, I’m sorry.” Classic Canadian, apologizes for something that shouldn’t need apology. Clearly I hadn’t brought my passport with me to a concert – it was safe in the tiny house. I moved out of the line and over into another line for pop (my new American friends died at the term – it’s soda!) feeling a bit defeated. I felt a tap on my shoulder and I turned around to find a girl that had been standing in front of me from line to line coming into the venue – I had noticed her dress earlier, totally cute and very Regina-chic. “Hey – we overheard – would it be weird if we bought you a drink?” My little heart. I’m supposed to be the nice Canadian! “Oh my gosh. Seriously?! That is so nice!” I follow her back and I’m introduced to her fiance, Dominic, and Dominic’s parents. They buy me a drink (“on us – no, seriously!”) and we get chatting about Regina and how I’m travelling alone. “We thought you were just at the concert alone – you’re like, alone-alone?!” We end up chatting about their upcoming wedding and I tell them I’m a wedding photographer. They have a friend doing their photos for the wedding, but “have you done an engagement session?” “Nope.” “Would you like to? On me – this is a cool enough story on it’s own!” We plan for the next day after my scheduled waterfall tour – “We can meet at the Mountain.” Oh, yes, so casually – let’s just meet at the mountain. I died.

Regina Spektor killed it. The venue was incredibly strict and wouldn’t let anyone take photos with their phones (I got angrily whispered at by an attendant) so I have zero evidence that it happened, but Camille, Dominic and family were only a few rows over and they can vouch! Regina had a few hiccups but humbly took them in stride, and after all these years to still be nervous performing speaks volumes to me – I don’t know that there will be a wedding day I won’t be nervous for, or even a meeting with clients where I don’t second guess myself. Her words of wisdom were “Maybe if I close my eyes this will be easier.” She felt her way back through to the melody and continued playing as if nothing had happened. I want to say that was another lightbulb moment for me – sometimes, following the instructions and protocol can get in the way of truly feeling what is right. I’d been so structured for so long attempting to be the best version of myself, when really all I need to do is close my eyes… refocus… and play. Needless to say I was a bit teary through her set, the weight of the last few months and the buzz of excitement of the next few days meeting in a rush of feels. It was a beautiful night.


I drove home to my tiny house and collapsed into (after climbing up to) bed. This was only barely the first day. Tomorrow was completely mine to spend as I wish. The feeling of freedom washed over me and I couldn’t quite believe that I was miles away from home, yet felt so absolutely comfortable, so calm, and so grounded. I drifted off to sleep knowing I’d wake to my own adventure.


To go back and read Part 1, click here.


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