19 Things To Do When It's Dreary in Portland

He writes in the font. She writes in this font.

Scene: Saturday night, Downtown Broadway, 9:45pm. It’s cold, rainy, and I lack the protection of a coat, which I am using to shield Megan and her camera from the slightly more than misty downpour. Apparently any drops of rain that hit her lense “ruins the shot.” I don’t know such things.

For the past thirty minutes we have hermit-crab shuffled up and down the street trying to get the perfect shot of the luminous “Portland” sign clinging to the side of the Arlene Schnitzer Concert Hall. Like a single organism, I help navigate my coat-covered better half and her tripod closer, then to the left or right, of the glowing letters that descend elegantly down the building. Ignoring the people, speeding cars and consequent puddle splashes; this is how we spend our weekend nights.

I hear a few “click-clicks” in rapid succession. Then, a little beanie-covered head emerges from under my coat. “I got it baby, thank you!” End Scene.

I can’t even imagine what we must have looked like to others, the thought of it definitely puts a smile on my face. Little moments like this also remind me of how lucky I am to have so much love and what a gentleman Guy is. It was alarming at first when he said, “Here, let me put my coat over you.” I’m sure my face looked contorted as I said, “but, won’t you be wet and cold?!” He simply replied with a “I’ll be okay.” It wasn’t until we were finishing up that he mentioned his fingers were starting to numb.

We were devouring frozen yogurt less than ten minutes later. Yes, I know, cold food in cold weather is counter-intuitive — we had a craving. Sitting at Tart Berry, spooning through our loaded creations of nuts, fruit, and maybe some chocolate-covered gummy bears, I asked Megan what people do here in the winter months.

She paused to think…

Portland’s incredible weather this summer spoiled me. I grew accustomed to the very late sunsets, warm days, and all the nearby hiking. Now that it’s getting a bit more chilly and the rain is less tolerable, Megan and I need to find new adventures in this great city.

Below is the list we started of fun things to do that offer warmth and moisture-protection. Please send us your suggestions as well! Throughout this winter season we will post about our adventures at the places below and perhaps spotlight some suggested by you.

In the meantime, here are the shots we got from that rainy night on Broadway, with a few from atop OHSU as well. Enjoy!



Winter Adventure List



  1. The Nutcracker at Keller Auditorium (Thank you, Mom, for buying us tickets!)

  2. Powell’s for a little book shopping — an obvious classic

  3. Portland Art Museum — We cannot wait to see the new Center for Contemporary Native Art

  4. Great Expectations  

  5. Christmas Ships Parade - We may need some hot cocoa and rain jackets for this one!

  6. Home Alone! — The Oregon Symphony Orchestra plays the score from this holiday classic at Arlene Schnitzer Concert Hall on December 19!

  7. Oregon Museum of Science and Industry

  8. Ice Skating - we might also be visiting the hospital this same night.  

  9. ChocolateFest!

  10. Blazers games! GO RIP CITY! - This one is not a new idea, but it is a favorite rainy season classic

  11. Toxic Avenger, The Musical

  12. Take the Tram (at night)

  13. Portland Night Market

  14. Pacific Northwest Photography Viewing Drawers

  15. Dance Classes - We are trying to take over the floor at wedding receptions - watch out!

  16. Levé Charity Ball 2015 - Saturday, December 12th 7pm til Midnight

  17. First Thursday

  18. The Book of Mormon

  19. Portland Winter Light Festival - Another one at OMSI