48 Hours in Portland, Oregon (Fall 2025)
There are few places I'd rather welcome fall than Portland, Oregon. Between cozy restaurants, independent bookstores, rainy streets, and a healthy dose of spooky season fun, it's the perfect city for an autumn weekend getaway. This particular trip had a little bit of everything: incredible food, local shopping, my very first Labubu, my best friend flying in from the East Coast, and one unforgettable night celebrating all things drag and horror!
If you're looking for a cozy fall itinerary packed with great eats and unique experiences, here's how we spent 48 Hours in Portland, Oregon!
48 Hours in Portland, Oregon
Stay @ The Hoxton Portland
We absolutely loved staying at The Hoxton. While the rooms are definitely on the cozier side, the location couldn't have been better for exploring Portland on foot, and the service? Truly 100/10. Every staff member we interacted with was warm, welcoming, and genuinely excited to help. Nestled in Old Town Chinatown, it's become one of our favorite places to stay in the city, and I'll absolutely be back.
Movie Date @ Regal Pioneer Place
Nothing says fall quite like a spooky movie! We kicked off the weekend by catching the newest Conjuring film before diving into the rest of our Portland adventures. It was the perfect way to set the mood for what turned into an unapologetically Halloween-themed getaway.
Dinner @ Din Tai Fung
It wouldn't be a Portland trip without Din Tai Fung! I happily introduced Maiya to my tradition with baskets of steamed buns, noodles, and enough dumplings to convince ourselves we should probably order "just one more." It's one of those places that somehow lives up to the hype every single visit.
Brunch @ Besaw's
Brunch at Besaw's was everything you hope a Portland brunch will be: cozy atmosphere, thoughtful seasonal dishes, and great service. It's the perfect slower start before a full day of exploring and my my my were our bellies FULL by the end of our time there! Pace yourself - the dishes are massive and you won’t be able to order just one! The pancakes are a must.
Shopping in the Pearl District
The Pearl District remains one of my favorite neighborhoods in Portland to wander. Naturally, our first stop was Powell's City of Books, where I never leave empty-handed. From there, we ventured over to Hawthorne to visit Portland Pop-Up, where I officially purchased my very first Labubu! Safe to say… I understand the hype now.
Dinner @ Tope
One of the biggest perks of staying at The Hoxton? Dinner is only an elevator ride away. Their rooftop restaurant, Tope, serves up incredible Mexican-inspired dishes alongside sweeping city views. It was such a fun atmosphere and the perfect place to settle in as the sun started to go down over Portland.
Dragula Season 666 Tour @ Roseland Theater
The highlight of the weekend - without question. As longtime Dragula fans, finally getting to experience the tour live from the very front row felt like a dream! The Boulet Brothers and the entire cast of monsters put on an unforgettable show that perfectly blended horror, glamour, artistry, and pure entertainment. If the tour ever comes anywhere near you, GO. Whether you're already obsessed with the show or simply appreciate incredible live performances, it's absolutely worth the ticket.
From the spooky movie kickoff to one final rooftop dinner and an unforgettable night at the theater, this trip was everything I love about fall wrapped into one weekend. Portland somehow manages to feel cozy, creative, and just a little weird in all the best ways - and that's exactly why I keep finding reasons to come back. Until next spooky season, Rose City!
