Portland, Oregon is a quirky city that has gained notoriety over the past few years for being a little “weird”. The pedestrian-friendly downtown area has bigger lanes for bicycles than cars and you’re more likely to eat out of a truck than a restaurant. Portland has the most breweries and independent microbreweries of any city in the world and the most strip clubs per capita. Oh and don’t forget that Portland voted to legalize marijuana. It’s kind of like Las Vegas but for hipsters.
Portland has become an ideal vacation destination in recent years as it offers nearby mountains for skiing, beaches for relaxing, plenty of waterfalls cascading into pristine rivers, and well-maintained hiking trails for all experience levels. The city has also earned praise for having a creative food scene, a plethora of craft breweries and wineries that rival those in Napa (but tastings are actually reasonably priced). Also lively beer festivals, farmers markets, lovely green space for all to enjoy, and down-to-earth locals.
And Portland is also famous for rain. Native Portlanders joke that the rain lasts from the day before Halloween (ruining those trick-or-treating plans) to just after the 4th of July (also ruining those BBQs). If you are planning on visiting Portland in the fall, winter, or even beginning of spring, follow our packing tips so you’re ready for the weather and all the other obscurities that “keep Portland weird”.
Quick Navigation Links
Disclaimer: This post may contain affiliate links – including Amazon, Airbnb, and others. If you make a purchase or booking through one of our links we may earn a small commission (don’t worry, it’s at no extra cost to you).
Portland, Oregon Travel Basics
Weather in Portland
Portland gets an average of 44 inches of rain on average every year. And an average of only 144 sunny days per year (the US average is 205). It only snows about 3 inches every year while the US average is 26. From about October until May you can pretty much count on dreary, overcast, grey days where it rains just enough to be annoying but not quite enough to inspire you to buy an umbrella.
But, on the bright side, all that rain means that the parks and forests in and around Portland are lush and beautiful for you to enjoy!
Preparing for your Trip to Portland
To prepare for your upcoming trip to blustery Portland load up on Vitamin D (because you’re unlikely to get any sun here), binge watch all 8 seasons of Portlandia, and be sure to start honing your hipster-spotting skills!
Where to Stay in Portland
Portland is home to some truly unique hotels that can suit any budget. Check out a few of our favorites here!
What to Wear in Portland in the Fall and Winter
It rains an average of 100 days out of the year in Portland and most of that is concentrated during the fall and winter months. The misty rain seems to be just enough to make you damp and miserable but not quite enough to force you to stay indoors or use an umbrella. Be sure to check the weather report prior to departing and bring plenty of waterproof attire so you don’t end up spending your vacation cooped up in your hotel room!
Pick up a pair of sturdy Hunter rain boots so your feet don’t get soaked while you’re out exploring the city. Casual is the standard dress code for Portland hipsters so don’t worry, you won’t feel out of place if you wear bright pink rubber boots.
The restaurant and bar scene in Portland is also super casual. The only bars that have a specified dress code are ones you don’t want to go to anyway. Bring some cute waterproof wedges like these from Sorel that you can dress up for a night out on the town!
Be sure to pack a lightweight rain jacket to throw on whenever you head outside. Something that is insulated, waterproof, and has a hood should do the trick. This one by Helly Hansen is super durable and will last you for many rainstorms.
Don’t forget to throw a compact travel umbrella in your suitcase for your trip to Portland. Supposedly most native Portlanders don’t use them (I do!) so you’ll be outing yourself as a tourist. But at least you won’t be soaked like everyone else.
Other Essential Rain Gear for Portland
There are countless amazing hikes just an hour or so east of Portland in the area referred to as the Columbia River Gorge. You’ll need to head this way to check out the tallest waterfall in Oregon – Multnomah Falls. Or if you’d rather stay in the city, there are a number of well-maintained trails in Forest Park – an enormous park situated right on the outskirts of downtown. A few of our favorite hikes outside of Portland include:
Read more about our favorite hikes in the Columbia Gorge here!
Waterproof Trail Runners
Pack a pair of comfortable hiking shoes that have a lot of traction and will keep your feet dry if you get caught hiking in a downpour.
Warm, Water-Resistant Jacket
It generally only snows a few days a year in Portland but regardless you’ll see trendy hipsters rocking puffy coats in bars all over the city. Pack one that is lightweight, compact, and water-resistant like this one by Mountain Hardwear. And throw it in your pack before setting off on your hike in case temperatures drop or the rain starts.
Pick up a few pairs of water-resistant, fleece-lined leggings to keep you toasty while hiking in the Columbia River Gorge. You’ll find that restaurants and bars in Portland are super casual so if you pair these with your Hunter rain boots and puffy coat you’ll fit right in!
Unfortunately Portland does not have an NFL team or a major league baseball team. But we still have plenty of sports teams that we get really, REALLY excited about. You should most definitely try to catch a game or two during your trip – you’ll have a blast!
Portland Timbers Gear
The Timbers are Portland’s MLS soccer team. The mascot is “Timber Joey”, a real-life lumberjack who saws chunks off of a huge log every time the team scores. If you get tickets for the “Timbers army” section, get there early to secure seats that aren’t behind a giant pole. And if you can’t get tickets, head to Uno Mas right near the stadium to watch the game on tv while munching on yummy tacos.
Show your spirit and bundle up with this Portland Timbers scarf!
Portland Trail Blazers Gear
The Trail Blazers are Portland’s NBA team and Damian Lillard is the star player on the team. You can usually find reasonably priced last-minute nose bleed tickets for games leading up to the playoffs. Their mascot is “Blaze the Trail Cat” which makes absolutely no sense whatsoever.
Pick up a knit beanie to keep your head warm and show your Portland pride!
Oregon Ducks Gear
You’ll have a bit of a drive if you want to catch an Oregon Ducks football game – the University of Oregon is in Eugene, about 110 miles south of the city. But the tailgating outside of Autzen Stadium is arguably the best in the nation! Plus they have a bar inside the stadium and will begin selling beer and wine in the concession stands this year. Their mascot is cute, cuddly Daffy Duck!
Rock some green and yellow gear to the game like the fresh rain jacket above or these adorable socks!
They say it “never rains at Autzen” but I would beg to differ. Best bring a vintage-looking spirited rain jacket, just in case!
“How did the hipster burn his mouth? He ate his pizza before it was cool.” Portland is a breeding ground for those who detest the mainstream, complain about gentrification, shop in thrift shops, turn their noses up at food that hasn’t come straight from the grass-fed farm, and are generally standoffish. Pick up The Hipster Handbook before your trip so you can emulate them if this sounds appealing, or spot and avoid them if it doesn’t.
Beard Maintenance Kit
A long, well-manicured beard is a staple for every Portland hipster and/or lumberjack. Plus it will help to keep half of your face warm in the cold wintery weather.
Buy a flannel shirt, but definitely not this flannel shirt! You must buy one that has been lovingly worn and then donated to a secondhand store because hipsters only shop at thrift stores.
Most hipsters don’t just want to be seen as cool. They also want to be seen as the intelligent, bookworm type. Someone who pours over Hemingway by day and stares blankly at abstract art pieces by night. You’ll need four eyes rather than just two to achieve this look.
A Host of Dietary Restrictions
No good hipster can go out for a meal and just eat off of the menu, that would be ridiculous!
Nothing gets the party started quite like a little vinyl Frank Sinatra. Bring your portable turntable and your dad’s favorite records to every social gathering in Portland and you’ll be the hit of the party!
Wearable Sleeping Bag
Nothing says “keep Portland weird” like wearing your sleeping bag into the bar! It’ll keep you snuggly warm and is also super convenient in case you drink too many craft IPAs and fall asleep on a park bench.
The most popular transportation method in Portland is bicycle and locals opt to bike rather than drive all year round, rain or shine. But bicycles aren’t exactly easy to pack or store so instead, invest in a hoverboard and cruise around the city in style!
Portland is a VERY liberal city and you’ll find that most Portlanders go out of their way to be sustainable (i.e. they use their own bike pedaling power to blend their raw veggie smoothies). If you try to shop at the local farmers market without your own reusable bag or if you request a straw with your cocktail you’ll probably get looked at with disgust and/or confusion.
Think you’ll want to drink a raw, organic juice or a cold brew coffee while visiting Portland? Don’t even think about using a plastic straw! You’ll be asked to leave the city. Just kidding but you’ll probably get a few angry stares. Don’t risk the public embarrassment and keep a stainless steel reusable straw on you at all times in case thirst strikes!
Reusable Shopping Bag
Shopping is one of the favored things to do in Portland among tourists. People even cross the border from neighboring states to get their hands on our goods. Know why? No sales tax! Nada. Zip zero. Be sure to save some time to shop till you drop during your visit but BYOB (bring your own bag).
Portland is famous for the hundreds of food trucks that you’ll find all over the city (and even in the PDX airport!). A few that you must try during your visit are The Grilled Cheese Grill, Potato Champion, and Koi Fusion. Most food trucks don’t have seating so your meal will be served with takeaway packaging – ideal for eating on the go but not so ideal for our landfills.
Don’t be shy about asking for your food in your own to-go container, they’ll be happy to oblige!
Reusable Water Bottle
The tap water in Portland is totally drinkable, no filtering necessary. Pack an insulated water bottle and fill up before heading out for the day. Hydro Flask even originated in Bend, Oregon so you’ll be buying local!
The craft beer scene in Portland is epic and once you find a brewery that you like you’ll most certainly want to buy more to-go. Pick up an insulated beer growler that you can fill up at the brewery and take back to your hotel to enjoy late night!
Here are a few of our favorite Portland breweries:
Don’t forget to read all about our favorite weird and wonderful things to do around the city of Portland!
Want more tips on things to see and do in and around Portland? Check out our favorite guides!