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

Take a fall foliage walk through Washington Park or Forest Park as the colors change. Stroll through piles of colorful, crunchy leaves on Portland hikes, like the Witches Castle hike.

2. Watch the Vaux Swifts fly into the chimney at Chapman Elementary

Check out the magical Swift Watch in September, as Vaux Swifts roost in the chimney at Chapman Elementary in NW Portland.

3. Go apple picking in Hood River or on the West side

Go east or west, but fall is for apple picking! You can do the Fruit Loop in Hood River through Parkdale. Favorite stops are Mt Hood Organics apple orchard (apple cider! honeycrisp apples!) and Kiyokawa Family Orchards. Bonus, stop at Solera Brewery or the new Mountain View Brewing.

4. Trail running in Forest Park

With miles of trails and millions of trees, Forest Park is the perfect spot to get a run (or walk) in and have a moment of zen away from the city.

5. Find your new favorite Portland coffee shop

Fall is for lazy weekend mornings finding your new favorite coffee shop. Without the guilt of needing to make use of a perfect summer weekend. Or go one step lazier and just nurse a cup of Trailhead Coffee at home.

6. Browse at Powell’s Books

Find your next fall read by perusing the shelves at Powell’s. I especially love checking out the wall of Bestsellers and Staff Picks. And accidentally buying one or ten too many books.

7. Pick the perfect pumpkin at Sauvie Island

Find your perfect pumpkin at a pumpkin patch on Sauvie Island. And then get distracted by hayrides, corn mazes, cow train, caramel covered apples, apple cider, and beer – optional ;)

8. Get lost in a corn maze

Haunted – or not – Sauvie Island has three farms to choose from with artistically crafted corn maze designs. Weekends or closer to Halloween are your times for navigating haunted mazes.

9. Renew your library card

Start making use of your Multnomah County library card. Especially now that you have more free time to stay indoors. Hello, fall. Plus, did you know you can check out Kindle ebooks and audio books for free? Yep!

10. Find your favorite comfort food in Portland

Hit up Screen Door for some Southern comfort food. Hello, mashed potatoes and gravy! Or Miss Delta on Mississippi.

11. Explore a new (to you) Portland park for some fall foliage

With over 200 parks and gardens in Portland, you can probably find one you haven’t visited. Like fall color watch at Columbia Children’s Arboretum (grown-ups allowed too) in Northeast Portland.

12. Taste the best Fresh Hop beer

Early fall is fresh hop season in the NW. Find your favorite fresh hop from Portland breweries like Breakside, Stormbreaker, and Hopworks. Yum – seasonal hoppy goodness! Or catch a fresh hop beer fest!

13. Welcome soup season

It’s officially soup season when the rain starts. Head to Luc Lac, Elephant’s Deli, and don’t forget all the pho!

14. Finding the best chocolate chip cookies

Hands down, Courier Coffee downtown has the best chocolate chip cookies in Portland. So good, we had them as our wedding dessert instead of cake. Yep, they’re that good!

15. Upgrade your cold weather sock game

Buying fun socks and tights (stripes, argyle, polka dot!) is just more fun from a sock store, like Sock Dreams.

16. Lean into tea season

Enjoy The Tao of Tea from the Lan Su Chinese Garden in Old Town.

17. Celebrate Oktoberfest at Prost!

Prost! is Portland’s German beer staple. From their original location on Mississippi, to their NE 28th Stammtisch location, and their brand new pub in Bend, Oregon. They usually celebrate Oktoberfest in fun ways! Block parties and pretzels!

18. Biking to Cathedral Park

Take a fall bike ride around the city. A ride out Willamette Blvd to the St John’s bridge and Cathedral park (one of my favorite Portland views) with views of the changing colors and the beautiful arches of the bridge.

19. Go to the soaking pool

Take a cold weather dip in the soaking pool at McMenamin’s Kennedy School or Edgefield (beer on the side please, and post-swim cajun tots!).

20. Order pie

Late-night pie, or maybe it’s not late, it just gets dark so early now. Anyway, a slice of seasonal pie and decaf coffee from Random Order (RIP!) or Lauretta Jean’s has fall written all over it.

21. Live music

Chilling to live music at the cozy Doug Fir Lounge and patio fires at Rontoms feels that much better in fall and winter.

22. Go apple tasting

The annual apple tasting festival at Portland Nursery is such a fun way to try tons of different apples. Probably canceled again because of COVID so you’ll have to go to New Seasons and DIY your own apple tasting festival!

23. Find a fall hike

Fall hikes in the Columbia River Gorge (Wahcella Falls! Eagle Creek!), with a stop in Cascade Locks Thunder Island or Gorges Brewing after.

24. Weekend biscuits and gravy

Warm biscuits from Pine State Biscuits or Gravy.

25. Watch a Blazers game

It’s basketball season again! And that means Blazers games. Whether you’re in the stands or watching at home or your neighborhood pub, like Migration.

26. Have breakfast at Multnomah Falls

Did you know you can eat breakfast at Multnomah Falls Lodge? Yep! Breakfast with a view!

27. Views from Pittock Mansion

Whether you drive or hike to Pittock Mansion, the views are unbeatable on a clear day.

28. Order speak-easy style cocktails

Rainy season is kind of drinking season in Portland. So catch up on your speakeasy drinks at Bible Club in Sellwood or Multnomah Whiskey Library.

29. Try a new indoor workout

With all the fall and winter drinking and eating, we could all use a new workout. Barre3 was started in Portland and las locations all around the metro area. Or try their at-home option.

30. Drink Chai lattes

Or pumpkin spice, but I’m gonna stick with a spicy chai from Extracto Coffee or a homemade chai.

31. Buy new ath-leisure pants

Trade up your summer shorts for some new athleisure clothes (yeah ok, it’s just another name for yoga pants) at Lululemon in the Pearl or PrAna on 23rd.

32. Take a cooking class

Cooking classes are such a fun indoor activity. Food and fun! Sur la Table has switched to virtual.

33. Order all the sweet potato fries

Fall is sweet potato fries season at Burgerville – and beyond.

34. Watch a movie at your favorite theather pub

Movie, beer, and popcorn at Laurelhurst Theater, please!

35. Learn something new

Take a class in something that interests you. It’s fall so it feels like back to school. PCC offers lots of community continuing education classes. Or something like Intro to Letterpress class at IPRC.

36. Try new Willamette Valley wines

New local wines from the safety of the weather. Check out ENSO or SE Wine Collective.

37. Go shopping Sellwood

Sellwood has so many interesting antique and vintage shops and spots to check out.

38. Find all the food carts with heated covered seating areas

It’s still food cart season if you can be warm and dry. The Cartopia pod on 12th, Piedmont Station and more.

39. Dreaming about Portland travel deals

Fall is for scoping deals on flights out of PDX to somewhere warm for a winter escape.

40. Order whiskey

Call it an autumnal whiskey and get a whiskey beer back at Produce Row or The Old Gold.

41. Watching a musical

Catching a musical or performance at Keller Auditorium.

42. Order all the Thai food

Having 250ish Thai restaurants to choose from. Among the best: Nong’s Khao Man Gai, Chaba Thai, Pad Thai Kitchen, Jade Teahouse.

43. Go to a live storytelling show

Backfence PDX storytelling shows!

44. Dress down for casual fall

Appreciate that a hoodie and jeans can pass for dinner appropriate in Portland.

45. Eat all the brunch

Massive weekend breakfasts at Jam and Besaw’s and Broder or wherever your favorite spot is.

46. Kiss your honey in our poorly lit streets

Why do we have such poorly-lit streets? It’s a Portland mystery.

47. Get ready for Oregon college football

Beavers and Ducks! It’s Oregon college football season. So get ready for the rivalries. Go sports!

48. Long dinners at fancy restaurants

Find something to celebrate and treat yourself to a fancy long dinner at Ava Gene’s.

49. Go cabin camping

You can still do some fair-weather end of season camping by staying in a yurt or cabin at one of Oregon State Parks. And Stub Stewart State park is only a 30-40 minute drive from Portland.

50. It’s pasta season

Order all the pasta at Grassa or Gabagool (RIP!) because rain is always an excuse for more carbs.

51. Discover new Portland music

Whether you’re going to show or scoping out new tunes and cute local goods from Tender Loving Empire.

52. Make happy hour be your dinner

Happy hour just seems like dinnertime in fall and winter because it’s already so dark out. So hh it up at Clark Lewis.

53. Watch a rainstorm from The Grotto

The views from NE Portland’s lookout, The Grotto, is the perfect place to watch a rainstorm roll through.

54. Write in a new journal

Fall is for new journals or notebooks and coffee shops are the place to write, like at cozy Coava Coffee.

55. Ride the train

Riding the train always feels like such a cold weather thing. And riding the train from Portland to Seattle is a fun trip.

56. Shop for bright accessories on Alberta or Hawthorne

Brighten up your fall look with bright and colorful bags and accessories to stand out from the grey.

57. Take pictures of the changing leaves

Is it really the first day of fall if you don’t Instagram a picture of changing leaves somewhere in Portland? Some favorite spots are Hoyt Arboretum, the Japanese Garden in Washington Park, and admiring all our Oregon fall foliage: Japanese maples and bigleaf maple.

58. Drink a hot toddy

Oh yes, it’s almost hot toddy season! The hot toddies at The Observatory are a favorite. Or anywhere you walked or biked to feels pretty great.

59. Buy all the bread

Bread, glorious bread — see Ken’s Artisan and Lovejoy Bakers.

60. Playing board games at coffee shops

While sticking around a coffee shop isn’t quite the same since COVID appeared, I do miss going to coffee shops for board games like Settlers of Catan at Floyds Coffee.

61. Drive a scenic route

I love fall scenic drives and beautiful waterfalls along the Historic Columbia River Highway and stopping at Sugarpine for softserve ice cream. Or take a weekend getaway for one of Oregon’s best fall hikes (and hot springs!).

62. Find the best hot chocolate

Don’t worry, I already found the world’s best hot chocolate. It’s at Timberline Lodge. Day trip!

63. Escape to the Oregon Coast

Speaking of day trips, head to the coast for a day trip, as there’s nothing like watching a storm right on the ocean.

64. Gear up for fall and winter activities

Fall is the perfect time to prepare for next season activities, with a trip to REI or Next Adventure.

65. Take photo booth pictures

Yeah, you can do this year round, but finding cozy photo booths around town, like at The Standard is just more fun in cooler weather.

66. Sing karaoke

Now that we actually want to be inside, rent a room and sing karaoke and order sake at Voicebox.

67. Eat donuts

Smirk at people standing in line in the rain, with umbrellas, at Voodoo Donuts and then go to Pip’s donuts.

68. Rainy walks

Rainy or non-rainy walks on Mt Tabor, looking at the city and all the fall colors.

69. Harvest in Oregon wine country

It’s harvest time for Willamette Valley wineries!

70. Walk over a Portland bridge

Walk over the Hawthorne bridge in the rain, and look back at our beautiful rainy city. Or any Portland bridge for that matter.

71. Order Cuban breakfast

Cuban breakfast and cafe con leche from Pambiche is a lovely way to kick off a fall day.

72. Catch up on Willamette Week or Portland Mercury

Pick your poison – WW or The Merc – and catch up on the latest Portland “news” over weekend coffee, while ignoring the rain outside.

73. Find your favorite Portland Lebanese

I’ll always be loyal to the veggie mezza and steaming hot pitas at Ya Hala.

74. Grown-up events at OMSI

One of my favorite fall things was events like OMSI After Dark and OMSI Science Pub at Mission Theater. Science + beer = awesome.

75. Plaid Portland

Yes, Plaid Pantry is fittingly the name of our convenience stores, but I do love scoping out the copious amounts of plaid around town. And appreciating the seemingly more fall-appropriate Portland bearded folk.

76. Cocktails downtown

It always feels a little swankier to be sipping cocktails downtown at a hotel bar (RIP Clyde Commons) or Teardrop Lounge.

77. Shop the Pearl district

Shopping for new cozy sweaters in the Pearl or other downtown Portland shops.

78. Organize a weekend pub crawl

I’m sure you can find something to celebrate this fall. Even if it’s just all the seasonal ales.

79. Peruse comics

Now that we have more time on our hands, go for a wander and peruse comics and Japanese toys at some Portland comic shops.

80. Order bread pudding

Stake out a spot at Crema with your laptop, and order bread pudding and coffee on a rainy day.

81. Wear colorful rain boots or jacket

Gotta have some fun in the rain. And if it’s time for a raincoat upgrade, check out the RAINS store. Yes, it rains so much here, a Danish raincoat brand decided to open a US store here. Makes sense.

82. Watch the Portland Marathon run by

The first weekend of October, is usually the Portland Marathon. Since the course goes through the city, it’s fun to watch some of the race. Especially neat is to find a spot to see the first handful of runners fly by!

83. Attend the Portland Book Festival

It was called Wordstock, and is now just the Book Festival. Or just cozy up with a new book at Oui Presse on Hawthorne (in the Hosford Abernethy neighborhood).

84. Plan out your December Portland activities

Most of December and the Christmas season is in fall. Yep! Confuses me every year! So decide what Christmas events you want to see in December.

85. Go to a holiday market

Crafty Wonderland, Portland Night Market, the Portland Flea. Holiday markets are kitschy, but festive.

86. Sample seasonal brews

You can go all out at the Holiday Ale Fest, or you can do a DIY version like a DIY beer advent calendar.

87. Start your Christmas shopping

Since most of December is technically fall, that means it’s time to start your Christmas shopping with Portland made gifts.