Halloween in Portland
Portland is a little weird on a normal week, but on Halloween week (Halloweek?) it is on a whole other level in the best way. We planned our Halloween trip to Portland with 3 things in mind: we wanted it spooky, we wanted to take a lot of pictures, and we wanted to explore as much of the city as we could in 3 days. When we took this trip in October of 2018, I wasn’t blogging as heavily as I am now, so almost all of the photos and videos we have are from Instagram stories. We spent 3 months researching and then asked our followers on IG for tips as well. We compiled a giant list and then took to Google maps to plan our routes, transportation, and order of events. It was absolutely perfect.
We rented a car only because we planned to venture outside the city one day to Saint Helen’s, but if we hadn’t done that, I think we would have been perfectly fine walking or Ubering around. Although late in the afternoon on Halloween, we got in the car and explored some neighborhoods (there’s so many pretty ones!) and checked out all the kids costumes who were trick-or-treating.
Stay
We stayed at the Hotel Rose Staypineapple in downtown Portland right on the river. It was perfectly central to so many things we wanted to see and do and even though we rented a car, we found ourselves walking quite a bit because it was so easy. It was pretty no frills but had a great restaurant called Bottle + Kitchen and there were often mini cupcakes and coffee waiting in the lobby. I kinda love a good cheeky sense of humor in a hotel, and got a kick out of our do not disturb sign. Each room comes with a stuffed doggy that helped ease the sadness of missing my real puppy.
They also have paid on site parking, which was great and they offer little yellow bicycles for rent! We didn’t rent them but I kinda wish we had. While Leo didn’t make the trip with us, they are a pet friendly hotel and offer the Pineapple Pup Package that includes a water bowl, treats, and a bed for your furry friend!
Play
I’ve mentioned before that I’m a meticulous planner when it comes to traveling. We like to HEAVILY research where we’re going, reading blog posts, searching Pinterest and Instagram to find all the best spots. We were only in Portland for 3 days, so I’m sure there’s a TON of things we missed, but here are all the little adventures we embarked on.
The Peculiarium
I was fascinated by the Freakybuttrue Pecularium the second I saw a photo of it on Pinterest. It’s essentially a gift shop and macabre museum all in one, featuring weird, scary, and just plain gross little exhibits, some of which you can interact with. One of my favorites was a big creepy dollhouse that looked dilapidated from the outside and on the inside was a full blown murder crime scene all made of doll house furniture. Gross? Yes. Cool? Totally.
They also had life size models of Krampus and a life size model bathroom that depicted a scene in which a victim’s organs had been illegally harvested. Something Jerry seemed really disturbed by but I was endlessly intrigued hahaha.
The Wandmaker’s House
On our second night in Portland, we visited The Wandmaker’s House Pop-up, which was a combination of a puzzle room and an immersive photo opp experience by The Meridian Adventure Co. It’s since closed, but The Meridian Adventure Co. is always throwing new pop-up events and are currently working on a new puzzle room experience. Make sure to follow them on Instagram to stay in the know!
Halloweentown
To be perfectly honest, we planned our entire Portland trip based on my childhood dream to see Halloweentown. 30 minutes outside of Portland, Saint Helen’s, Oregon is the home of the original filming of the Disney movie that I absolutely loved as a kid (& apparently parts of Twilight? I don’t know, I wasn’t a fan of that franchise). The town celebrates their 15 minutes of fame every year with a slew of activities and sometimes even a celebrity guest appearance by the actors! It’s a teeny tiny town that is mostly contained to one main street and anchored by a large government building that doubles as a museum that was City Hall in the movie. It’s fun seeing the businesses that were in the movie and seeing what they are in real life (for example the dentist office with the big tooth outside from the movie is actually an insurance office, but they put the big tooth prop out every Halloween).
Saint Helen’s has a ton of activities during the month of October but we went on a random day during the week when there was nothing happening so we could just casually walk around and snap pictures. Make sure to follow The Spirit of Halloweentown on Instagram to keep up!
The Shining at The Kennedy School
On Halloween Night, we visited the Kennedy School for a late night showing of The Shining. The Kennedy School was built in 1915 and is literally an old abandoned school that has been converted into hotel but it has maintained a ton of the old fixtures. There are small bars in old classrooms (one is literally called The Detention Bar), restaurants in the gym, and a movie theater in the auditorium. Next time we visit, I definitely want to stay here. There are 57 guest rooms with private bathrooms- some of them used to be classrooms and still have the original chalkboards! The walls through the hallways are covered with original artwork and historic photographs. It’s old, a little creepy, and the perfect place to spend Halloween.
The White Stag
I’m a little embarrassed to tell you how long we stood on a bridge waiting for this sign to be lit to get this picture hahaha. We had been planning it for weeks. Jerry staked out the are on Google Maps before we left in order to find the perfect spot to take this picture. The area surrounding the sign was a little sketchy (we actually witnessed two homeless men get into a brawl and one threw the other’s jacket into the street on a 32 degree night- Jerry got it back for him) but I never felt unsafe. I’m not sure if it counts so much as an activity, but it was for us! We are pretty obsessed with photos, so we went back to this sign 3 times at 3 different times of day and night to make sure the shot was perfect. That probably sounds silly, but we had a blast.
Eats
Departure
Y’all. We ate our way through Portland, AND I AM NOT SORRY. We had done a ton of research and lots of people told us we had to check out Departure which is an absolutely gorgeous restaurant with a rooftop bar that gives you access to some of the best views of the city. It’s pricey…really pricey… and one of those fancy restaurants where you’re still hungry when you leave (we got donuts on the way back to the hotel), but I’d still stop by for a drink at the bar to soak in the sights.
Pine Street Market
This was another spot that was highly recommended and we LOVED it. It’s a large space with tons of different counter food options. We got burgers at Bless Your Heart Burgers and topped them off with Cubra Libre Slushies and soft serve from Salt & Straw. Absolutely delish and the walk back to the hotel afterwards was very necessary lol.
Cartopia
Cartopia is a pod that takes up about a city block comprised entirely of food trucks and food carts. We went on day when it was sprinkling a bit, but they had covered seating and outdoor heaters so we were still comfy. I highly recommend Potato Champion- it’s a poutine food truck that has crazy unique combinations (think PBJ Fries…WHAT?!). I got the Satay Poutine and it was to die for.
The Cookie Dough Cafe
The Cookie Dough Cafe is exactly what it sounds like: edible cookie dough in a variety of flavors served in scoops like ice cream. It was unbelievably delicious and we both ate until we were almost sick. Seriously, when will Reno get on the cookie dough train?!
Old Town Pizza
Pizza is always good, but I actually picked this place because of it’s story. The building that houses Old Town Pizza & Brewing used to be a hotel (in fact, the window where you order your pizza used to bee the check-in desk) and it sits directly on top of the infamous Shanghai Tunnels that were used to house kidnapped sailors in the early 1900s. Legend says it is haunted by a prostitute named Nina who was thrown down an elevator shaft after sharing information with traveling missionaries. We sat in the back in a booth that used to be an elevator shaft where Nina is said to have carved her name into the brick. I told Jerry this story while we waited for our pizza and he was thoroughly freaked out, but me? I love a good ghost story and I think Nina and I were both giggling at him ;)
Oh & the pizza was bomb.
Voodoo Donuts
A trip to Portland would not be complete without a trip to (one of) Voodoo Donuts’ locations. I personally think they lived up to the hype, but many people will tell you there’s better options. However, after dinner at an overpriced restaurant with teeny weeny portions (see above), there’s nothing quite like biting into a warm giant donut shaped like a voodoo doll.
Slappy Cakes
Slappy Cakes was our final stop before we headed to the airport to go home. It’s a do-it-yourself pancake/breakfast spot and we had a BLAST. You can order whatever toppings you like, along with different pancake batter flavors, and whipped cream and you make them yourself on a griddle at your table. We were so excited for this that we laid in bed the night before scrolling Pinterest for tutorials on pancake art. We were definitely over-confident because they all looked terrible…but they were delicious!
This video of Jerry’s “cat” pancake still makes me giggle.
