Holidays + Seasons Portland

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

Fall Leaves rainbow in Portland

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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. As Oregon battles intense wildfires this year, fall and cold wet weather can’t come soon enough. Bring on the rain! Jump Ahead:

87 Things to Do in Fall in Portland, Oregon:

  1. looking at Portland fall colors with a stroll through crunchy leaves in Forest Park (like the Witches Castle hike)
  2. watching the Vaux Swifts fly into the chimney at Chapman Elementary
  3. apple picking in Hood River and doing the Fruit Loop (honeycrisp apples from Mt Hood Organics please!)
  4. annual apple tasting festival at Portland Nursery (canceled 2020)
  5. lazy weekend mornings nursing a cup of Trailhead Coffee
  6. browsing at Powell’s books
  7. picking a pumpkin at a pumpkin patch on Sauvie Island. Hayride, corn maze, cow train and caramel covered apples optional ;)
  8. making use of Multnomah County library, (now that you have more free time to stay indoors)
  9. southern comfort food (hello, mashed potatoes and gravy!) at Screen Door
  10. fall color watch at Columbia Children’s Arboretum (grown-ups allowed too)
    Red leaves in Portland, Oregon fall
  11. rocking colorful rain boots or rain jacket
  12. fresh hop season is here – seasonal hoppy goodness
  13. navigating a corn maze at Sauvie Island
  14. it’s officially soup cart season again, SoupCycle if you need your soup fix delivered.
  15. chocolate chip cookies at Courier Coffee (missing you Courier!)
  16. buying fun socks and tights (stripes, argyle, polka dot!) at Sock Dreams
  17. enjoying The Tao of Tea from the Lan Su Chinese Garden
  18. it’s finally scarf season again
  19. Portland Zombie walk
    rainbow leaves at the Childrens Arboretum
  20. steaming hot pitas with your veggie mezza at Ya Hala
  21. biscuits at Pine State Biscuits
  22. chilling to live music at the cozy Doug Fir Lounge and patio fire at Rontoms and Basecamp
  23. rainy season is drinking season. Catch up on speak-easy style cocktails.
  24. cold weather dip in soaking pool at McMenamin’s Kennedy School or Edgefield (beer on the side please, and post-swim cajun tots!)
  25. rediscovering your favorite riding boots for fall’s first First Thursday
  26. Saturday breakfast (nope, not Sunday brunch) at Multnomah Falls Lodge
  27. trading in your summer shorts for new yoga pants at Lululemon in the Pearl
  28. eco-conscious fashion week production? Portland Fashion Week
  29. science + beer = awesome. OMSI Science pub at Mission Theater
  30. tiny cups of drinking chocolate at Cacao
  31. staying indoors with OMSI After Dark
    Pumpkins on Sauvie Island
  32. sampling seasonal brews at Holiday Ale Fest (probably not for 2020)
  33. catching a musical at Keller
  34. indoor workouts that hurt so good, Barre3 (started in Portland fyi)
  35. Backfence PDX storytelling shows – we miss you!
  36. cooking classes — for food and fun
  37. shooting hoops and watching a game at Spirit of 77
  38. swimsuit shopping for a winter getaway
  39. fall hikes in the Columbia River Gorge
    eagle creak hike in Columbia River gorge
  40. staking out a spot at Crema with your laptop, bread pudding, and coffee on a rainy day
  41. cozing up with a new book at Oui Presse
  42. chai lattes at Extracto Coffee or homemade
  43. scoping out copious amounts of plaid on NE 28 Ave (& the appreciating the seemingly more fall-appropriate Portland bearded folk)
  44. movie, beer and popcorn at Laurelhurst Theater
  45. trying new wines from the safety of the weather
  46. antique and vintage shopping in Sellwood
  47. learning something new, Intro to Letterpress at IPRC
  48. appreciating that a hoodie and jeans can pass for dinner appropriate in PDX
  49. 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
  50. it’s sweet potato fries season at Burgerville
  51. whiskey (& whiskey beer backs) at Produce Row and The Old Gold
  52. dreaming over the latest deals for a winter escape from Portland
  53. food carts with heated seating areas, Pyro Pizza at Cartopia
  54. bright, colorful bags and accessories to stand out from the grey
  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. perusing comics and Japanese toys at downtown shops
  68. playing boards games at coffee shops, Settlers of Catan at Floyds Coffee
  69. bread, glorious bread — see Ken’s Artisan and Lovejoy Bakers
  70. hot toddies at The Observatory
  71. fall drives along the Historic Columbia River Highway and stopping at Sugarpine for softserve.
  72. because when it’s raining, it seems perfectly reasonable to stop at your 3rd coffee shop of the day, Barista
  73. barista latte Portland
    crowded cocktail sipping at Clyde Commons
  74. shopping for new sweaters in the Pearl
  75. Cuban breakfast at Pambiche
  76. world’s best hot chocolate at Timberline Lodge
  77. preparing for the coming winter activities with a trip to REI or Next Adventure
  78. escaping to the Oregon Coast, as there’s nothing like watching a storm right on the ocean
  79. photo boothing at The Standard
  80. karaoke and sake at Voicebox
  81. walking over the Hawthorne bridge in the rain, and looking back at our beautiful rainy city (or any Portland bridge for that matter)
  82. catching up on Willamette Week or Portland Mercury (pick your poison) over weekend coffee, while ignoring the rain outside
  83. smirking at people standing in line in the rain, with umbrellas, at Voodoo Donuts and then going to Pip’s donuts
  84. foot massages with friends at The Barefoot Sage seems so much more deserving when the sun isn’t shining at 5pm
  85. harvest in Oregon wine country
  86. organizing a weekend pub crawl to catch all the seasonal ales.
  87. starting your Christmas shopping with Portland made gifts.
portland beer

Fall Events in Portland

Fall is officially September 22 through December 21, 2020, although we often think of the autumn season as the months September, October, and November. As the bulk of the December and the “Christmas season” seems so wintery, doesn’t it!? Here are our favorite Portland fall events. For a full list of events in Portland, check out Travel Portland’s list. Here are the big ones.

Fall leaves in Portland October

Portland in September

>>More about Portland in September – events, weather, and things to do.

Portland in October

>>More about Portland in October – events, weather, and things to do.

Portland in November

  • Portland Book Festival (was Wordstock) – November 5-21, 2020
  • Christmas Tree Lighting – Pioneer Courthouse Square

>>More about Portland in November – events, weather, and things to do.

Portland in December

>>More about Portland in December – things to do and Christmas events.

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.