Our Cozy Fall Getaway to Portland, Oregon

The first time that my mom ever met Eric, my boyfriend, was also the first time he and I flew together. Being born and raised on the East Coast, I found the Fall season in Los Angeles to be a bit lackluster, so I booked myself a ticket to Portland, Oregon. I told my mom and boyfriend that either of them were welcome to join me. It became an impromptu couples trip as they both said yes and my mother’s boyfriend, who just so happens to be from Oregon, joined our entourage as well. He has a sister and brother-in-law living in Portland who kindly took us all in for our short stay.

In my mind, it is hard to rival a New England fall, but Oregon was up for the challenge. In our few days there in October of 2019, we went on an underground ghostly tour, got lost in a corn maze, found ourselves in the scenes of films, and saw elk while experiencing a coastal sunset.


We started the trip off the way all trips should commence - wine tasting. I think anyone who knows us could agree this is also the perfect first way for Eric to get to know my mother. Just a short walk from Kelly and Jason’s, our gracious hosts, we were able to enjoy delicious local wines and cheeses at Blackbird Wine Shop. While I’m not what one would consider a “foodie,” sometimes food and drink is the heart of a trip, and while in Portland we ate very well. For my mother, the highlight will be the local tamales brought by a vendor door to door. For Eric, it would be Ground Breaker Brewing.

Eric has celiac disease, meaning he will get very sick if he consumes gluten or if it is cross contaminated with his food. When I was planning the trip, and was by no way whatsoever using it as bait to try to coerce him into booking a flight to come with me, I came across Ground Breaker Brewing, a completely gluten free brewery and restaurant. The two of us had a date night here where we split a large flight of every beer in the place and delicious tacos. This was his first time at a gluten free brewery and it was a very memorable experience. Now, we are very grateful to get to pick up this beer at our local liquor store in Los Angeles which always reminds us of this trip. Pro tip, when booking trips that you are going on with significant others, strive to plan something in advance that is geared towards their interests because it definitely makes them more likely to go along with whatever shenanigans you like that they could go without. Which brings me to...

I have a small obsession with going to historic places that are known to be haunted. The stranger part? I don’t even believe in ghosts; but something about the hidden and hushed histories of these less than common tourist attractions intrigues me. The Shanghai Tunnels underneath Portland show a dark side to the city's past. Passageways that ran from Old China Town to the water were used to hold and transport those who were shanghaied (kidnapped), before being sold into slavery. The tunnels are thought to be haunted and while we did not experience the supernatural, the tour was interesting and might help us answer a question or two in a future trivia game.

In addition to my affinity for haunted tours, I always seem to find myself at craft markets in cities around the world, Portland being no different. The Portland Night Market is a quarterly event that hosts the best craft and food vendors from around the area in a beautiful and hipster setting. Getting local art and crafts is an amazing way to support small businesses when you are traveling. These purchases act as the perfect gift to give someone you wish had been traveling with you, or as a memento to treat yourself with. The outdoor beer garden was also a great venue to meet up with friends of ours who now live in the area.

While most of our time in nature was spent outside of the city's border, we did head to Macleay Park to hike to Witch's Castle. The grounds are thought to be haunted giving the this two-story stone structure its nickname, though it is officially called the Stone House. It was built in 1930 by Portland Parks and Recreation with the intent to be a ranger station and bathroom but was abandoned after a storm. Since then, it expanded its history into becoming a high schoolers party haven, hence the graffiti. The hike was only half a mile through a beautiful forest and well worth it.

Nature Right Outside the City

With beautiful changing leaves and lovely craftsman architecture, Portland puts you in the cozy fall vibe. Just outside of the city to the east, Multnomah Falls supersedes any waterfall I have yet to experience on the west coast. The waterfall is named after a local tribe of Chinookan people, was formed over 15,000 years ago, is fed mainly by underwater springs, and is 620 ft tall, making it the tallest waterfall in Oregon. A short walk up a paved trail took us to Benson Bridge where we had an amazing view of the waterfall looking both up and down. While this was gorgeous with the autumnal colors, I guarantee it is worth the trip year round.

From here, we took a scenic drive up Larch Mountain. At the top, there was a parking lot and a short trail just a little over half a mile that led us to Sherrard Point. We were lucky enough to have a clear day, allowing us to view Mt. Rainier, St. Helens, Adams, Hood and Jefferson. This is my favorite kind of hiking; minimal effort required but a huge payoff.

Saint Helens

I enjoyed our short excursion to Saint Helen’s, a small town thirty minutes north of Portland, but my mother and Eric have never let me hear the end of it. The town square of Saint Helens was the backdrop for my favorite Halloween film, Disney’s 1998 classic Halloweentown. Each year, the town celebrates the season with The Spirit of Halloweentown; a ceremonial lighting of the giant pumpkin. While I considered the festivities classic and quaint, my companions felt they were cheesy and boring. This might only be worth the trip for the superfans.

Speaking of superfans, one might say that I’m in the top 5% of the world's most obsessed Twilight fans. I know that right about now you are judging my taste in pop culture, but I don’t want to hear it. Halloweentown wasn’t the only franchise to grace the town, but Bella Swan’s House from the Twilight movies is nestled in its woods as well! I was extremely excited to see this in person, but really you just hop out of your car, take a photo, and then move on. At least my mother couldn’t judge me on this one because she is secretly a fan as well. When visiting, please make sure to be respectful and stay off the property as this is a residential home and they are probably sick of all of us nerds showing up.

One thing that Eric and my mother actually agreed with me on being enjoyable was the Pumpkin Patch on Sauvie Island. The farm had stalls to get food, hot cider, local goods, free hay rides, an animal barn, and, of course, pumpkins. My favorite part was going through the corn maze with my mom and boyfriend which makes me nostalgic of childhood when I would always go to the one in my hometown. For me, getting to participate in fall activities made the trip exactly what I was looking for.

Cannon Beach

The Pacific Northwest coastline is in a league of its own and one of my top three favorite places in the world. On our last day, we drove out of the city to Cannon Beach. The sky reflecting on the wet sand made for a beautiful walk along the beach. We headed up to Ecola State Park to get an elevated view and were greeted by some elk. This was a view and moment I will never forget.

For dinner, we checked out Driftwood Restaurant and Lounge. The outdoor seating around a personal fire was beautiful and we had amazing seafood, a must for me while on the coast. This place was perfect for us as they had gluten free options for Eric and a decadent bloody Mary, a must for my mother.

Our final stop was at Fort Stevens State Park. This short excursion allowed us to see sunset at both the ocean and the mouth of the Columbia River. Once again, the wet sand reflected the dazzling colors of the sky. We walked for quite a while, soaking it in, not wanting the trip to end.

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