Chasing the Leaves: A Weekend in Portland, Oregon

Fall is my absolute favorite season. I love the coziness, the sweaters, the leaves, and the weatherly encouragement of indoor activities. Unfortunately, LA in October is HOT – I mean shorts, tank tops, and constant sweating hot. So this year, I decided to book a ‘fall-cation’ to Portland, Oregon with my friend Ella.



We took a morning flight and landed around 10am. The Portland airport is super laid-back (especially compared to LAX) and it helped us settle in to what would be a very chill weekend. We took an Uber to our AirBnB (located in the SE). Our driver was playing intense Classical music that almost seemed to (intentionally?) match the scenic views of woods and overcast skies – we were definitely not in LaLa land anymore! After we got settled into our home for the weekend, we went for a walk to explore the city. We were practically skipping with joy wearing our layers and scarves, and delighting dramatically over every multicolored leaf we saw.

  • We headed to the Saturday Market (in the SW) and shared as much food as we could physically manage from a variety of food trucks. The theme of the weekend was “why wasn’t I born with a extra stomach?!” As there isn’t sales tax in Portland, we couldn’t believe how much food we could get for $10.
  • We browsed some stores in Pioneer Square and made the mandatory tourist stop at “Voodoo Doughnuts” – great branding, surprisingly low prices, creative combos, but average doughnuts if you ask this Tim Horton’s-loyal Canadian.

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  • Powell’s City of Books – This bookstore occupies a full city block and claims to be the largest in the world. If many of your childhood “friends” were book characters (like mine were), then this place is exactly as magical as it sounds.
  • Deschutes Brewery – We noticed a strong sense of “family/life integration” in Portland. Everyone was out and about, just living – eating good food, drinking beer… and babies were there too! It was the stuff dreams are made of. I would definitely recommend this ‘family-friendly’ brewery, and in terms of food, you can’t go wrong with the pretzel.

On the walk home, we loved how relaxed and peaceful it felt (hard to believe it was a Saturday night). It was quieter walking across a main street in Portland than the traffic typically is outside my suburban valley bedroom window back home.


  • Cafe Broder – Yelp led us to this Swedish breakfast gem. There was a bit of a wait to get inside but it was well worth it. I had the apple fritters with pork sausage and it was one of the most delicious breakfasts I’ve EVER had. Enough said.
  • Hike to “Punchbowl Falls” – A couple of good friends of mine from Toronto recently moved to Portland and I was so happy to spend time with them! They took us on a hike to see some of Oregon’s natural beauty – this was a definite highlight of our trip. (If you do this hike, wear layers and sturdy hiking shoes.)


  • After warming up at our AirBnB, we walked to Division Street and had some delicious hot apple cider from Tortoise + Hare (Awesome pod of food trucks can be found at 2880 SE Division Street).
  • We walked along Division Street, checking out the various shops (no shortage of bars or coffee shops available here).


  • We ate dinner at the Bollywood Theatre – DELICIOUS, authentic Indian street food in a comfortable and trendy environment at an excellent price. I recommend ordering the paneer kati roll.
  • We heard that Oregon is known for its pinot noir so we went to Division Wines to try a few (their sampler includes 3 generous pours for $14!). I loved everything about this place: the wine, the coziness, the wood counters, the classy French music, and the fact that we were the only people there!

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  • Sweedeedee – Courtney brought us here for brunch and, boy oh boy, is it epic. The vibe is homey yet hip. Think ironic record player and cassettes mixed with homemade bread and a wreath your mom would like. I had an OUTRAGEOUS egg sandwich on homemade bread and we shared some of their famous honey cake.
  • Then, sadly, it was time to head to the airport for our quick flight back to LA.


To sum it up, if you live in a warm climate and are seeking a weekend getaway, Portland is a great choice. It provides just the right amount of chill in the air, and you’ll definitely see some leaves a changin’. It’s a cheap 2 hour flight direct from LAX, yet getting off the plane, you’ll be transported into a completely different vibe (and season!). Where else can you walk down the street and hear both live didgeridoo AND bag pipe players? Friendly cats roam freely, the smell of wood burning fireplaces is abundant, and the air is so fresh you’ll think you’ve been on a cleanse. It almost feels like you’re in a heart-warming Disney Channel Halloween movie. It was a short trip, but it completely recharged me, and I’d love to go again!

Thanks for reading.

❤ Kailea

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