October 2025

October is truly the perfect time to visit Portland, Oregon. The city comes alive with rich fall colors, crisp air, and cozy vibes that make you want to grab a pumpkin spice latte and explore every corner. We spent a quick weekend in the heart of downtown Portland, and it was everything we could have hoped for – a mix of great food, history, and a few spooky surprises.

🏨 Where We Stayed

We stayed at The Benson Hotel, and it was absolutely stunning. The moment you walk in, you’re greeted by a grand lobby with a glowing fireplace, intricately carved wooden staircases, and a breathtakingly detailed ceiling. It’s one of those hotels that instantly transports you back in time, yet still feels luxurious and comfortable. Our King Suite came with a spacious living room and elegant decor – plenty of room to relax after a day of exploring.

🍽️ Midtown Beer Garden – Portland’s Ultimate Food Truck Haven

We kicked off our trip with lunch at Midtown Beer Garden, and honestly, it was one of the highlights of the weekend. Imagine a huge open-air space surrounded by every kind of food truck you could dream of, from artisan coffee and handmade dumplings to authentic tacos and Italian desserts. In the middle of it all, there were long wooden picnic tables where everyone gathered to enjoy their food finds together. It was the perfect way to soak up Portland’s laid-back, foodie culture.

🍩 A Sweet Stop at the Original Voodoo Doughnut

After exploring downtown a bit more, we couldn’t resist making a stop at the original Voodoo Doughnut in Old Town Portland. Even though Voodoo has only been around since 2003, it’s become a cultural icon featured everywhere from MTV to Good Morning America.

We grabbed a mix of their most famous and seasonal treats, including the Grape Ape, Maple Blazed Blunt, Banana Cream, Oh Captain My Captain, Glazed Old Fashion, and of course, the classic Jelly-Filled Voodoo Doll. Each one was delicious and surprisingly not overly sweet. The flavors balanced perfectly, making it easy to enjoy more than one (or two… or three!).

👻 Exploring the Spooky Side of Portland

The next day, with Halloween right around the corner, we decided to lean into Portland’s spooky side. We started the afternoon at Old Town Pizza & Brewery, grabbing a late lunch and one of their craft beers before joining the Shanghai Tunnels Ghost Tour.

The 90-minute walking tour took us deep underground into Portland’s historic tunnels, once used to transport sailors and illegal goods. The guide shared eerie ghost stories, historical tidbits, and local legends as we explored. The tour wrapped up with a beer tasting in the tunnels – definitely a fun and unique Portland experience!

While we enjoyed the tour overall, we think it could vary a bit depending on your guide. Ours focused a bit more on personal anecdotes, but the tunnels themselves and their stories were fascinating and worth seeing.

🍻 Dinner and Drinks at Kells Irish Restaurant & Pub

After the tour, we made our way to Kells Restaurant & Irish Pub, a Portland staple with a warm, welcoming atmosphere and live music that fills the room. The food and drinks were excellent, hearty Irish fare with a Pacific Northwest twist. We had hoped to visit their cigar lounge downstairs, but it was closed during our visit, which just means we’ll have to come back next time!

Final Thoughts

From Portlands rich history and creative spirit to its incredible food scene and cozy autumn charm, Portland gave us a great weekend. Whether you’re visiting for a weekend getaway or a longer trip, there’s something for everyone here.

If you’re thinking about planning your own trip to Portland, I’d love to share more tips and recommendations to help you make the most of your visit!

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