Portland has two very different seasons which are often just designated as “summer and winter” or “summer and fall/winter/spring” — you can usually tell who is a local by how specific they’ll get about what the season is (writing this as I enthusiastically called late January “pre-spring”). Summer, according to Oregon legend, doesn’t start until July 5, and will end sometime between Labor Day and Halloween, at which time everything is winter until the flowers start blooming and locals once again wear t-shirts, sundresses, and sit on patios for their coffee and cocktails.
All that is constant is the footwear. Year-round we wear hiking boots like Timberland, Merrell, and Danner that can handle some muddy bits and rain puddles. Those will change to good trail-running shoes or hiking shoes in the very warm months (“summer”), but few of us choose sturdy sandals meant for trails (like Keen or Teva) unless we’re planning to get into water. Most of the year we also wear wool socks, usually in layers. We can’t say enough about the importance of comfortable and warm boots/shoes and socks in the winter. Even if you’re not planning on hiking more than a few miles, it’s imperative for your happiness and the rest of your weekend/week/trip for you to wear the kind of shoes you could walk 10 or 15 miles / 18-30 kilometers in. Most of our trips don’t include enough hiking to destroy your toenails/heels if you’re breaking in new boots, but we still recommend having walked a while in your own shoes before you wear them to hike up and down muddy hills.
Layers, layers, layers. Any time of year we suggest layers, especially in the parts of the year you might not expect to be chilly. Even July and August can include cooler mornings than you expect, so a sweater or sweatshirt in the summer and a couple of warm (preferably wool) layers in the colder months will keep you from shelling out cash for sweatshirts at the gift shop while you’re out and about. Not that gift shop sweatshirts aren’t a great souvenir!
Make one of those layers a raincoat with a hood. You’ll notice that Portlanders are lots less likely to use umbrellas than most of the world. Instead, we opt for often-colorful raincoats with amply-sized hoods. If the weather the week you’re traveling has more than a minimal (<30%) chance of rain, you’ll be happy for a hoodie.
Scarves/hats/gloves or mittens. Look at the low temperature predicted for every day you’re traveling, not the high. If the low temperatures are in the 40s Fahrenheit / single digits Celsius, pack a warm scarf, a warm hat, and warm gloves or mittens. If you are acclimated to much warmer climates, you might want to do that if the low temps are anything below 60F/16C, which means most of the year.
Go for comfort and think about how your clothes would feel if they got very wet. Unless you’re traveling in July and August, when rain is very unlikely, coarsely woven and tight fitting pants (like jeans) can be very uncomfortable if you get caught in a rainstorm. Likewise, some polyester coarse weave garments or thick wide legged sweats can be super heavy and miserable if you end up getting soaked. We usually opt for some kind of breathable lightweight tights on very cold days (yep, wool again) and skirts/shorts and lightweight, not-to-tight and not-too-loose pants when it’s between 40 – 60 F or 8 – 16 C.
Dress for the low temperatures, with layers you can shed in the late afternoons. I know I’ve already written this but check the low temperatures and remember that places you are visiting outside the city, or even within it, like the Pittock Mansion viewpoint and parts of Forest Park, can be chillier and windier than the center of the city. I use a metric of five degrees cooler for every 1,000 feet of elevation gain (2-3 degrees C for 300 meters), which is very very approximate but usually a good guide. Also, the waterfalls and ocean can be 10 degrees F / 5 degrees C cooler without any other factors, just because of the cool air coming from the water itself.
Is it summer? Embrace it! If it’s warm get comfortable with loose-fitting tops and running shoes. Maybe you’ll end up with a group of new friends to hang out with (as in the photo above: a bunch of solo travelers who chose to hike and bike together after meeting at the hostel!). We love to see you smile!