The Best Time to Visit Portland According to a Local

When you mention Portland, the first thing people think of is rain (with coffee and beer coming in at a close second). And, though it is often overcast, it’s not nearly as rainy as you might expect.

However, the not-always-sunny weather is a reality you’ll have to accept if you’re visiting the city outside of summer, and if rain and “gloomy” skies are really that big a deal for you, maybe you should consider Phoenix instead. 

But for all you cool cats who aren’t gonna let a little precipitation stop you, the best time to visit Portland, Oregon will somewhat depend on the weather. Fortunately, because us Portlanders are no strangers to rainy/chilly/overcast days, we’ve made sure there’s PLENTY to do all year round, both indoors and out.

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The Best Time to Visit Portland: A Complete Guide

With a place as awesome as Portland, there’s really no bad time to visit, but the seasons will affect what you’re able to do (and what you’ll want to do) when you’re here.

The nice thing about the city is that it rarely gets really cold or really hot, and while climate change is changing this, it’s more or less accessible and comfortable year-round. 

When planning a trip, the best time to go to Portland really depends on how flexible you are, knowing that in the dryer months you can spend more time outside and in the wetter, colder months you’ll be indoors more often.

The Great Umbrella Debate

I believe in umbrellas.

This may not sound like a controversial opinion, but in Portland it is.

Many of my fellow locals are vehemently anti-umbrella and claim that’s how you spot a tourist.

However, I’m today to give you permission to carry one!

Sure, if it’s only sprinkling it’s easier to put on a good raincoat and not mess with an umbrella, but if you’ll be walking any distance in town I’m all for them.

I think it’s dumb how many Portlanders shun umbrellas. There—I said it! 

The Best Time to Visit Portland: A Breakdown by Season 

In this section, we’ll go through the four seasons, and what they offer visitors. We’ll also give you a pros / cons list to help you make your decision on when to visit Portland.

Summer in Portland 

Summers are often the best time of year to visit Portland, but they’re getting progressively hotter, and in recent years it’s not uncommon to see several days over 100 degrees.

In my youth (or even 10 years ago) I couldn’t recall a single summer day that topped 100.

Yet, summers in Portland remain magical with average temperatures in the 80’s and very little rain. This means you can do practically anything in and around the city and count on great weather.

Art Walks: A great way to explore some of Portland’s trendiest neighborhoods is attending one of its many art walks. First Thursday is in the chic Pearl District and runs late April through October. First Friday is in the up-and-coming Central Eastside and runs year-round, but you can catch live musical performances April through October. And don’t forget the rowdiest art walk out there, Last Thursday, in the Alberta Arts District that runs June through August—seriously, things get a little wild there.

Pedalpalooza: Bike fun all summer long! This is an all-volunteer, summer-long event featuring hundreds of group bike rides. Some are smaller and more relaxed while others attract hundreds of costumed riders for late-night shenanigans pedaling off to undisclosed locations for secret dance parties. I’ve been on a handful of Pedalpalooza rides over the years and they’re all great fun!

Sauvie Island: I’ll feature Sauvie Island a couple times in this guide because it’s the gift that keeps on giving. Sauvie Island sits just north of Portland, and summertime is full of u-pick berry and fruit stands, fantastic live music at Topaz Farms under the historic oak tree, hiking (try this one that also offers beach access you can’t reach by car), and swimming! My favorite swim spot is Collins Beach, but do note it’s a clothing-optional area. If you’re really lucky you may even see the Spirit of Sauvie Island! Wanna know more? You’ll have to go and find out for yourself!

Festivals Galore: Summer is festival season, and there’s no lack of options in Portland. I’ve highlighted some below in my month-by-month guide, but a few standouts are the Cathedral Park Jazz Festival (and I don’t even really like jazz), the Blues Festival at Waterfront Park, Oregon Brewers Festival because we Portlanders like our beer, PDX Live for huge musical artists playing downtown at Pioneer Courthouse Square, and the countless street fairs throughout town (my favorites are the Mississippi and Hawthorne fairs.)

Pros and Cons of Visiting Portland in the Summer

Pros:

• The weather, duh.
• Tons of festivals and outdoor events.
• Portland has lots of great outdoor spaces with parks, bike paths, and great beer patios.
• Easy to get around the city by foot, bike, or public transit and ditch the car.

Cons:

• The crowds. Because Portland is so rad, it sees a lot of tourism in the summer and basically everywhere you go (especially on weekends) will be packed. This affects how long you’ll have to wait in line, how long it takes to find a parking space, and how far ahead you have to book a hotel or rental.

Fall in Portland 

If anything, the effects of climate change have made fall in Portland even more lovely (though that’s no reason to think its consequences are in any way positive—sigh).

Practically though, it means we see spectacular late summer weather throughout September and even into early October. September temperatures are typically in the 70’s with only a little rain. October and November will see temperatures in the 50’s and 60’s with considerably more rain, but usually not enough to prevent you from having fun.

For those who have time to travel outside of summer, fall is the best time to visit Portland, Oregon.

Hiking: In my opinion, fall is hands down the best season to go hiking and camping in the area. Gone are the 90+ degree days, the mosquitos, and the crowds. What’s left are crisp mornings, warm days, and parking spaces when you need them. The snow has yet to reach the Mount Hood hikes; the waterfalls are starting to gush again; the world is as it should be. 

Harvest time: There’s nothing I love more than “sweater weather” and all that comes with it. Head out into the Gorge in October for the Hood River Valley Harvest Fest or the Hood River Hops Fest. Pop down to Mt. Angel for Oktoberfest for bratwurst, beer, lederhosen, and my favorite—the weiner dog races! Or the best cultural festival in town, the Polish Festival for pierogies and polka!

TBA Festival: Portland is a town of artists and creative types, and one of the best embodiments of this is the Time Based Art (TBA) Festival that runs for two weeks in September. See local artists come together for music, theater, fine-art, and wild avant-garde performances you couldn’t even dream up. The idea behind this event is that the art and audience come together for a unique experience that only exists in the time and space of the moment. 

Swifts: Every night in September about an hour before sunset, you can watch these migratory birds at Chapman Elementary School in NW Portland. Be amazed as literally thousands of swifts spiral down into the school chimney to roost for the night. It’s almost impossible to describe how cool this is.

Pros and Cons of Visiting Portland in the Fall 

Pros:

• Early fall weather is ideal for most activities, especially if you’re heading out into nature. I’ve been called a “greenhouse flower” because I don’t like to be too hot or too cold, and the fall in Portland is just that—the perfect temperature to do anything. 
• Kids are back in school so it’s considerably less crowded.

Cons:

• While the weather is still pleasant enough well into November, it will get more unpredictable, but this just means carrying extra layers and a raincoat (or umbrella!) with you.

Winter in Portland 

Winter is undoubtedly the wettest season of the year, so if you visit during December, January, or February plan on bundling up.

A good raincoat and waterproof shoes will go a long way for making what could be a wet, miserable day into a fun adventure.

It rarely gets very cold in Portland in the winter and daytime temps are usually in the 40’s, but some days dip into the 30’s. In the last few years, we’ve also had a few days of snow, but it’s almost always short-lived.

True, a lot of winter Portland activities involve drinking (you gotta keep your body warm somehow!), but there are plenty of non-alcohol-involved options like old movie theaters, music venues, arcades, roller rinks, museums, shops, or restaurants to keep you busy. 

Whale Watching at the Coast: The gray whale migration on the Oregon Coast runs from mid-December to mid-January as these massive creatures head south to Baja California. Although whales can be spotted year-round, winter is the best time as there are roughly 25,000 of these puppies who make the annual trip. Plus, my very favorite time to visit the coast is the winter when rates for ocean-front houses are at their lowest.

OMSI: The all-time best indoor Portland activity is the Oregon Museum of Science and Industry (OMSI, pronounced “ahm-zee”). Hands-on science activities, legitimately cool exhibits, the Omnimax theater, and “OMSI After Dark” for science fun with booze!

Oaks Park Roller Rink: Another blast from my past that’s still alive and well—the one and only Oaks Park roller rink. Who doesn’t love roller skating?! This place is stuck in time in the best way possible, and if you look closely you can almost see 10-year-old Diana rocking high-side ponytail careening around the corners. As a bonus, you can also see the incomparable Rose City Rollers at The Hangar right next door!

Mountain Fun!: Go skiing, snowboarding, or tubing at one of Mount Hood’s three ski resorts: Mount Hood Meadows, Ski Bowl, or Timberline. Winter is also a great time to rent a cabin on the mountain, curl up next to a fire, or play board games with good friends!

Pros and Cons of Visiting Portland in the Winter 

Pros:

• No crowds.
• Cheaper rates on hotels and vacation rentals.
• See the city in a new way that the fair-weather tourists miss out on.

Cons:

• Cold and wet—can’t get around it.
• Having a car is (almost) essential. 
• If it does snow, the city and its inhabitants do not know how to deal. No one knows how to drive in the snow and we don’t have enough plows, so the city basically shuts down, even if it’s only a few inches. If you’re coming from a place that really sees snow, please make fun of us—we deserve it.

Spring in Portland 

Springtime in Portland can still be quite rainy, but it’s starting to warm up. Average temperatures are in the high 50’s to low 60’s, and the rain is more like showers so if you can find temporary shelter, it won’t stop you for long.

Plus, when the sun does break free, the whole town pops their head out to bask in its rays. The flowers and cherry blossoms brighten up the city and it can seriously be the best time to travel to Portland.

Timbers and Thorns Season: Soccer fans (or anyone who just likes to have fun) can become a part of the Timbers or Thorns Army. Games start in March and continue through the summer at Providence Park which is right downtown, making these games extremely easy to get to via public transportation.

Waterfalls and Wildflowers: The waterfalls run year-round in the Gorge, but the flow drops off considerably in the summer. So, if you want to see these babies at their peak, springtime is the way to go when the snow runs off makes them truly spectacular. Wildflowers typically start springing up in April or May, but note that for the most popular hikes like Dog Mountain, you’ll need to get a special permit.

Farmers Markets: Nearly all the neighborhood farmers markets open up in May (the PSU Farmers Market is the only one that runs year-round). Most of these feature live music, food carts, local artisans, and of course—delicious local produce! A great option if you’re staying in a vacation rental and can cook a few of your own meals. 

Pros and Cons of Visiting Portland in the Spring 

Pros:

• Pretty decent weather—not too hot or too cold and the rain is only a mild hindrance.
• Springtime festivals like St. Patrick’s Day and the Tulip Festival are a blast!

Cons:

• Be wary of extra large crowds during spring break which is the last week of March for Oregon and the first week of April for Washington. This primarily affects the beaches, but can also make some “family” activities like OMSI, Multnomah Falls, or Oaks Parks prohibitively busy. 

So, What is the Best Time to Visit Portland? 

When to visit Portland, Oregon??? It depends!

No, I don’t get a cut from the city’s coffers for every tourist I convince to come in the middle of winter—I truly believe Portland is worth visiting year-round.

That said, it really depends on what you want to do and how flexible your to-do list is. 

When you plan a trip for fall or spring you gotta be ready for rain, although you may be surprised by beautiful sunny days. Winter warriors can pretty much count on wet days, but with the right gear you’ll stay dry. If you want to experience Portland’s food scene and see great live music, then winter or early spring allows you to avoid crowds and get into all the best restaurants without having to make reservations weeks in advance.

The Best Time to Visit Portland to Experience the Outdoors 

Portland is perfectly positioned with easy access to the Oregon Coast, the mountains (hello, Mount Hood!), and the Columbia River Gorge, making it one of the best “big city” destinations that also doubles as an outdoor getaway. 

The Gorge is known for its waterfalls, wildflowers, and hiking and the best time to see them in their finest form is the spring. However, because most of the hikes stay under 3,000 feet in elevation, they’re accessible throughout much of the year.

For the snow lovers, Mount Hood boasts three ski resorts and you’ll want to plan your trip in winter or early spring to get your fill of these.

Summer and fall will give you the best coastal weather and overall hiking, but you’ll have to accept the bugs and crowds that come with it. 

The Best Overall Time to Visit Portland 

Because I’m being forced to choose, I’d say the best time to visit Portland, Oregon is early fall for the great weather and lack of crowds. This generally means September is the best month to plan a trip, but you might be pleasantly surprised by October too.

Key Portland Festivals & Events by Month  

In this section, we’ll go through a sort of calendar of events by month in Portland.

Portland in January

Portland Music Month: A great remedy to the cold, gray Portland winters is hitting the town, shaking your bootie, and listening to live music. Not only does this month-long event promise shows every single night, but a dollar from every ticket sold goes to the nonprofit, MusicPortland Bridge that provides grants to local musicians. Venues all across the city host events, with over 100 shows to choose from!

Portland in February

Winter Lights Festival: Intentionally held in the “worst time” of year, the Winter Lights Festival is held in early February to bring communities together during the dark days of winter to shed much-needed light into the city. It’s free and usually cold, but it’s always the coolest thing I see all year (think light-based art installations a la Burning Man—and many are interactive!).

Portland in March

Worst Day of the Year Ride: Generally held mid-March, this costumed bike ride is meant to be done in the rain, but that’s part of the fun! There’s live music, free snacks provided by local vendors, a costume contest, and everyone gets together afterwards for beer!

Portland Dining Month: Portland Dining Month has been on hiatus for the 2021 and ‘22 season, but should return in 2023. Each March, dozens of Portland’s nicest (and spendiest) restaurants participate in this month-long event offering prix fixe dinners for a very low price (in 2020 it was $33/person for a three-course meal). This is one of the best ways to tour the best of Portland dining without breaking the bank, and it’s a springtime only event!

Portland in April

Wooden Shoe Tulip Festival: Located in Woodburn, about 45 minutes south of Portland, the Tulip Festival is a must-see event. It runs from mid-March through April and during this time, you’ll see Instagram accounts plastered with multi-colored fields of flowers as far as the eye can see. It’s breathtaking to see in person and a picture just doesn’t do it justice. 

Portland in May

Crafty Wonderland: Crafty Wonderland has become synonymous with the DIY spirit of Portland. They have two public markets held at the Convention Center, one in May and the other in December. They also have two brick-and-mortar stores, one in downtown across from the library and the other in the Alberta Arts District that feature quality, locally-made crafts. Great for one-of-a-kind Portland keepsakes and gifts that aren’t your typical touristy crap.

Portland in June

Portland Rose Festival: This annual festival kicks off each year on Memorial Day weekend and runs for three weeks into June. Opening night features a free performance by the Oregon Symphony, fireworks, and the start of CityFair at Waterfront Park. Not to be missed are the Starlight Parade (preceded by the Starlight Run—a 5k costume run along the parade route) and the Grand Floral Parade with exquisitely decorated floats and high-school marching bands!

Portland Pride Festival: June is pride month across the country and Portland’s festivities are always off the hook and capped off by a Pride festival in Waterfront Park. Yes, the west coast is very progressive and Portland is always prideful, but it’s nice to see the city turn up the volume during June.

Portland in July

World Naked Bike Ride: Have you ever watched a herd of 10,000 naked people riding bikes past you down a busy city street? Admittedly, it feels a little weird at first, but sooner than you’d expect you grow accustomed to it and the naked body once again becomes normalized. Pretty soon you’ll start to wonder why you’re the dumb shmuck who’s still wearing clothes. This is one of the most fun, body-positive events you’ll ever experience. All levels of nakedness welcome. Purportedly, Portland turns out the largest crowd for this in the world—not surprised.

Portland in August

Adult Soapbox Derby: A very fun—and free—event! Come for the beer, costumes, crashes, and good times! Held each year on Mount Tabor in SE Portland since 1994, this is one of those city events that everyone can enjoy.

Pickathon: Since 1999, this has been the local music festival to be at. A four-day event held at Pendarvis Farm in Happy Valley, just 25 minutes from downtown Portland. For maximum fun you should camp out, but you can also go for the day and rotate among the seven stages to see musicians, comedians, DJs, authors, or even a yoga session! Great for adults, kids, and adults with kids.

MusicFestNW (Project Pabst): If you want to hear some summer tunes, but don’t feel like leaving the city, MusicFestNW is for you! Typically held the last weekend of August, this music festival brings huge names to a two-stage venue at Waterfront Park. Ride your bike or take the bus into downtown, then party hard all night long!

Portland in September

Portland Dragon Boat Races: Though you can catch a glimpse of the dragon boats during the Rose Festival in the summer, the official races are in September. Teams come from all over the world to participate in this two-day event that has local vendors and a beer garden at Waterfront Park. 

Portland in October

Portland Film Festival: If there’s a better way to spend a rainy afternoon or evening than going to the movies, I don’t know what it is. The Portland Film Festival runs for two weeks in mid-October, bringing hundreds of independent films to the city including Q&A sessions with the filmmakers themselves.

The Pumpkin Patch: Sauvie Island is a favorite destination for Portlanders in the fall for pumpkin patches and the iconic Maize. Even if you can’t bring home and carve pumpkins, there’s nothing more “fall like” then spending the day at the pumpkin patch, getting lost in the corn maze, petting farm animals, sipping apple cider, going on a hayride, and soaking in the last sunny, cool days before winter sets in. Each year the Maize has a different theme and you can check out aerial pictures to see all the hard work and artistry that goes into making it. 

Portland in November

Blazer Games: The Portland Trail Blazer season is in full swing by November, and you can usually snag cheap, nose-bleed seats day-of. The Moda Center has a MAX (light rail) stop right next to it, making this a perfect rainy-weather activity that you don’t need a car for! Pregame at nearby Ex Novo Brewing Co. or the newly-opened and wonderfully-named Sports Bra, a sports bar dedicated to women’s sports.

Snow Sports: Although it varies each year when Mount Hood will see significant snow, you can almost always bet on the lifts running by Thanksgiving. November is the perfect time to dust off the old skis or snowboard (or rent gear from Next Adventure in Sandy) and hit the slopes!

Portland in December

Portland Saturday Market: True, the near 50-years-running market is open most of the year, but it’s in the holiday season that it really shines. It’s open every Saturday through December and always on the few days leading up to and including Christmas Eve for the “Festival of the Last Minute.” 

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