Your Essential Checklist for a Real Portland Fall

Lauretta Jean's Pie
Lauretta Jean's Pie | Ashley Marti
Lauretta Jean's Pie | Ashley Marti

Autumn has fallen on the City of Roses, and along with it, about a few million gallons of rain. For most Portlanders, it’s a return to the city they fell in love with. For others, it’s a gray wasteland devoid of joy. Here’s the best way to get through the rainy season, whether you’re a pluviophile or phobe.

Pick pumpkins on Sauvie Island

A time-honored Halloween tradition, picking pumpkins from the farm on Sauvie Island is a great activity for couples, families, or groups of friends. When asking a Portlander what to do in fall, it’s usually the first thing they tell you. Just remember: It’s Sauvie not Sauvie’s.

Get lost in an epic corn maze

While you’re on the island getting your future jack-o-lantern, make some time to check out the corn maze. It’s not just an essential fall activity, it’s an essential Portland activity, period.

oktoberfest portland
Oktoberfest | Courtesy of Mount Angel Oktoberfest

Pick an Oktoberfest party (or 10) to attend

Speaking of beer, Portland loves throwing Oktoberfest parties. Strap on your lederhosen, grab a yard of beer, and celebrate your German heritage, whether or not you have it.  

Drink whisky at the Library

The Multnomah Whisk{e}y Library has a roaring fireplace, so you can sip on a Scotch or bourbon while keeping things toasty and cozy. It also happens to be one of the best whiskey bars in the city.

multnomah county library
multnomah county library | Underawesternsky/

Go to an actual library and pick out a book to get you through fall

The Whisk{e}y Library is great, but so is the Multnomah County Library system. In fact, it’s often considered one of the best in the country. You can spend hours here peering through books and hiding from the rain. And best of all, it’s free.

Hit up one of our many haunted houses

Portlanders love Halloween (because it’s the best holiday, duh). There are tons of haunted houses set up around the city, so grab your friends and find out which one’s the scariest, and which one is just 60+ floors of David S. Pumpkins. FrightTown gives us a whole block of scares, while The Fear PDX has six spooky locations.

Find a new favorite cup of coffee

The Northwest is famous for two liquid masterpieces: coffee and beer. And Portland is no exception, with coffee shops scattered on every corner. While many of them have emulated Stumptown’s minimalist aesthetic, there are plenty of cozy, comfy spots to curl up in a big chair and sip a cappuccino in. Some of our favorites include Palio Dessert & Espresso House, Common Grounds, Blue Kangaroo, Rocking Frog, and Coffee Time. Or, if you like to hang with cats whilst sipping your latte, check out Purringtons Cat Lounge.

Find out where the best foliage is and go to it

Thanks to the rainy weather, Portland has magnificent foliage. In summertime that means a verdant canopy over the city, but in fall it’s brilliant flame-colored hues. Go for a walk on Mt. Tabor or Forest Park between bouts of rain and take in the autumn leaves.

Townshend's Tea
Townshend's Tea | Townshend's Tea

Drink tea at Townshend's

Not a coffee person? Portland still has you covered with some great tea shops, especially Townshend's Tea, which offers cozy, relaxing furniture and excellent tea at each of its four locations.

lauretta jean pie
Jenni Kupelian

Eat a damn good slice of pie

It’s never too early for a slice of pumpkin or apple pie. Lauretta Jean’s and Random Order Coffeehouse & Bakery are both great spots... where you can also snag a boozy or caffeinated drink (or both).

Go to the greatest book store in the country

Head to Powell’s Books and read a book or two while sipping a coffee (naturally). Then buy a stack of them like you're a squirrel packing away nuts for winter.


We mean the film festival, of course. Nothing rings in a Portland fall like watching strangers (and occasionally people you know) bone on film in hilarious, sexy, and almost terrifying ways.

mount hood
Mount Hood | tusharkoley/shutterstock

Get in a last minute hike... if you can

Fall is usually a great time to hit those gorgeous hikes you missed in the hotter weather, which won’t be as crowded as they were in August. However, with this year’s Eagle Creek fire possibly still burning, you’re not as likely to be able to make your favorite hike. All the more reason to take in the ones you can, while you can. Head west to Saddle Mountain for the day, or go check out the Timberline trails around Mt. Hood.

Watch the Vaux’s swifts divebomb Chapman School

Every year as they migrate south, the Vaux’s swifts swarm by the thousands into the chimney of Chapman School to roost for the night. It turns out, birds can be entertaining. Pro tip: It makes a great first-date spot.

marukin ramen
Marukin Ramen | Jannie Huang

Eat soup

It’s broth weather, go get some of the city’s amazing pho, or slurp up some ramen noodles, one of Portland’s newest and best food trends. Marukin and Afuri are great spots for Japanese noodles, while Ha VL and Phở Hùng are some of the best places for a bowl of Vietnamese soup.

hood river
hood river | Rigucci/Shutterstock

Get outta here and go someplace with sun

SAD is a real thing. Get out of town for a while, even if it’s just to Hood River.

Volunteer at a vineyard and earn free wine

The Willamette Valley and Columbia Valley are packed full of vineyards, all of which need help picking grapes in the harvest season. Chances are, you know someone who knows someone who works with Sokol Blosser, Penner Ash, Brooks, Teutonic, Hazelfern, Phelps Creek, or one of the other countless wineries that could use a hand. You’ll likely get a bottle or two for your help.

Sign up here for our daily PDX email and be the first to get all the food/drink/fun Portland has to offer.

Alex Frane is a Portland native, and thinks the rainy days are a perfect excuse for a good whiskey drink. Follow him at @franiacdrinks.