Fall in Portland: 87 Things to Do (Rain or Shine!)

portland red leaves fall

As Portland bids adieu to another glorious season of sunshine, here are 87 reminders of why Portland is still a great city to be in autumn. Since the transition back to rainy season can be tough for even the most seasoned Pacific Northwesterners, I’ve put together a list of reasons to embrace the rain autumn yet another year. In no particular order, here are 87 things to do in puddle season (aka fall in Portland). You may notice this list has a slight eating and drinking bend to it — it’s a good way to pass the time — and while not everything on this list can only been done in fall, it’s a pretty good time to try a few new things. And we’re off…

Note: this post has been updated for 2020. As Oregon battles intense wildfires this year, fall and cold wet weather can’t come soon enough! Bring on the rain!

87 Things to Do in Fall in Portland, Oregon:

Red leaves in Portland, Oregon fall
  1. looking at Portland fall colors with a stroll through crunchy leaves in Forest Park
  2. enjoying The Tao of Tea from the Lan Su Chinese Garden
  3. looking forward to a second season of Portlandia (arriving in January)
  4. rocking colorful rain boots and a Columbia rain jacket
  5. lazy weekend mornings nursing a cup of Stumptown in bed
  6. meandering about Powell’s books
  7. making use of Multnomah County library, (now that you have more free time to stay indoors)
  8. chocolate chip cookies at Courier Coffee
  9. annual apple tasting festival at Portland Nursery and apple picking in Hood River – honeycrisp apples from Mt Hood Organics please!
  10. it’s officially soup cart season again, SoupCycle if you need your soup fix delivered.
  11. buying fun socks and tights (stripes, argyle, polka dot!) at Sock Dreams
  12. southern comfort (hello, mashed potatoes and gravy!) at Screen Door
  13. it’s finally scarf season again, (au revoir to shopping for vintage scarves at Lodekka Dress Bus, we loved you!)
    Double decker dress shop
  14. Portland Zombie walk
  15. steaming hot pitas with your veggie mezza at Ya Hala
  16. biscuits at Pine State Biscuits
  17. chilling to live music at the cozy Doug Fir Lounge and patio fire at Rontoms and Basecamp
  18. rainy season is drinking season. Catch up on speak-easy style cocktails at Central and Secret Society
  19. fresh hop season is here – seasonal hoppy goodness
  20. cold weather dip in soaking pool at McMenamin’s Kennedy School or Edgefield (beer on the side please, and post-swim cajun tots!)
  21. rediscovering your favorite riding boots for fall’s first First Thursday
  22. Saturday breakfast (nope, not Sunday brunch) at Multnomah Falls Lodge
  23. trading in your summer shorts for new yoga pants at Lululemon in the Pearl
  24. eco-conscious fashion week production? Portland Fashion Week
  25. science + beer = awesome. OMSI Science pub at Mission Theater
  26. tiny cups of drinking chocolate at Cacao
  27. staying indoors with OMSI After Dark
  28. navigating the corn maze at Sauvie Island
    Pumpkins on Sauvie Island
  29. picking a pumpkin at the pumpkin patch on Sauvie Island (hayride, cow train and caramel covered apples optional ;)
  30. sampling seasonal brews at Holiday Ale Fest (probably not for 2020)
  31. catching a musical at Keller
  32. indoor workouts that hurt so good, Barre3
  33. Backfence PDX storytelling shows – we miss you!
  34. cooking classes — for food and fun
  35. shooting hoops and watching a game at Spirit of 77
  36. swimsuit shopping for a winter getaway
  37. fall hikes in the Columbia River Gorge
    eagle creak hike in Columbia River gorge
  38. staking out a spot at Crema with your laptop, bread pudding, and coffee on a rainy day
  39. cozing up with a new book at Oui Presse
  40. chai lattes at Extracto Coffee or homemade
  41. scoping out copious amounts of plaid on NE 28 Ave (& the appreciating the seemingly more fall-appropriate Portland bearded folk)
  42. movie, beer and popcorn at Laurelhurst Theater
  43. trying new wines from the safety of the weather
  44. antique and vintage shopping in Sellwood
  45. learning something new, Intro to Letterpress at IPRC
  46. making pumpkin pie
  47. appreciating that a hoodie and jeans can pass for dinner appropriate in PDX
  48. having 250ish Thai restaurants to choose from. Among the best: Nong’s Khao Man Gai, Pok Pok, Chai Thai, Pad Thai Kitchen, Jade Teahouse.
    Nongs food cart Portland
  49. it’s sweet potato fries season at Burgerville
  50. whiskey (& whiskey beer backs) at Produce Row and The Old Gold
  51. dreaming over the latest deals for a winter escape from Portland
  52. food carts with heated seating areas, Pyro Pizza at Cartopia
  53. bright, colorful bags and accessories to stand out from the grey
  54. homemade apple sauce and canning
  55. massive weekend breakfasts at Jam and Besaw’s
  56. kissing your honey in our poorly lit streets
  57. riding the train from Portland to Seattle
  58. Oregon college football (and the rivalries)
  59. taking pictures of the changing leaves at the Japanese Garden and admiring our Oregon fall foliage
    Japanese garden in Portland
  60. end of season cabin camping at Stub Stewart State park
  61. discovery new Portland music (& cute local goods) at Tender Loving Empire
  62. long dinners at Beast and Ava Gene’s
  63. pasta at Gabagool or Grassa because rain is always an excuse for more carbs
  64. the view and watching a rain storm for the lookout at The Grotto
  65. writing in your journal at Ristretto Roasters
  66. Happy hour seeming like dinner because it’s already so dark out @ Clark Lewis
  67. flannel sheets
  68. perusing comics and Japanese toys at downtown shops
  69. playing boards games at coffee shops, Settlers of Catan at Floyds Coffee
  70. carbs, glorious carbs — see Ken’s Artisan and Lovejoy Bakers
  71. hot toddies at The Observatory
  72. visiting the Museum of Contemporary Craft
  73. because when it’s raining, it seems perfectly reasonable to stop at your 3rd coffee shop of the day, Barista
    barista latte Portland
  74. crowded cocktail sipping at Clyde Commons
  75. shopping for new sweaters in the Pearl
  76. Cuban breakfast at Pambiche
  77. world’s best hot chocolate at Timberline Lodge
  78. preparing for the coming winter activities with a trip to REI or Next Adventure
  79. escaping to the Oregon Coast, as there’s nothing like watching a storm right on the ocean
  80. photo boothing at The Standard
  81. karaoke and sake at Voicebox
  82. walking over the Hawthorne bridge in the rain, and looking back at our beautiful rainy city (or any Portland bridge for that matter)
  83. catching up on Willamette Week or Portland Mercury (pick your poison) over weekend coffee, while ignoring the rain outside
  84. smirking at people standing in line in the rain, with umbrellas, at Voodoo Donuts and then going to Pip’s donuts
  85. foot massages with friends at The Barefoot Sage seems so much more deserving when the sun isn’t shining at 5pm
  86. harvest in Oregon wine country
  87. organizing a weekend pub crawl to catch all the seasonal ales.
portland beer

What’s your favorite thing about fall in Portland?

fall in Portland, hikes, leaves, bridges, pumpkins and always rain.

Originally published in 2011. Updated for 2020, but leaving pre-COVID fun because next fall… Photos by Geecy, sirgious, Darin Barry, Nick.Fisher, rupak anto, gabriel amadeus, star5112 and myself.

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