One of the most common question I get asked is “what is the best time to visit Portland, Oregon?”

The question is fair, considering our reputation for rain (and more importantly food and beer). Folks want to take advantage of the good stuff without feeling stir crazy after three days cooped up in a hotel.

That’s where I come in. I’m a lifelong Portland local and there’s nothing I love more than sharing my beloved hometown with visitors. I’ve lived through all four seasons many times over and have learned a thing or two about the best time to visit Portland.

So without further ado, let’s get to it.

Visiting Portland but don’t know where to stay? I have you covered. Here’s a roundup of the best hotels in Portland. Short on time? Here’s my favorite hotel, hands down.

Tips for visiting Portland for the first time

Pack a rain jacket, regardless of the predicted forecast. If you’re visiting Portland for the first time then you’ll want to take advantage of the great outdoors. As such, a visit to the epic waterfalls in the Columbia Gorge is non-negotiable, and you’ll want a rain jacket for that adventure. Here’s my tried and true classic.

A note on wildfires. Wildfires are on the rise and most locals have learned to anticipate them during summer (even fall). Growing up, wildfires were not a consideration to daily life in Portland, but now? They’re practically guaranteed. If you’re visiting during the summer months, know that nearby areas may be closed off due to wildfires. I’ll cover this more shortly below.

The city is going through growing pains. I’m anticipating (with bated breath) the snarky remarks about Portland going to hell in a hand basket. Rent prices tell me otherwise, but I’d be doing you a disservice by claiming we’re back to our regular levels of quirkiness. Portland is changing, evolving, and trying to solve the heartbreaking homelessness apparent in the City of Roses.

Now, as longtime readers know, I’m the first to admit that I don’t have a solution to the complicated world of homelessness. As such, I don’t feel right complaining because I’m not contributing to improvements simply by bitching.

But for first time Portland visitors, it’s helpful to know that you will see homelessness in certain pockets of the city. Has it ever stopped me from enjoying my evenings or taking date nights? Heck no. But it always stirs a conversation, so I want to point it out.

Best Time to Visit Portland, Oregon

Summer is the best time to visit Portland

Daily average temperatures: June (73°) | July (80°) | August (80°)

I’m not usually one for definitive statements, but in this case it applies: Summers is the best time to visit Portland.

Now I know that some locals will disagree with me on this. The heat! The wildfires! And it’s true, wildfires are definitely on the rise and our summers are way warmer than they used to be (we didn’t even consider an AC until last year), but I stand by my statement.

When compared to other major US cities, Portland in the summer has a lot going for it. Our summer temperatures tend to hover in the 80’s and both early mornings and late evenings tend to cool off substantially. But the best part? Well, it’s the lack of mugginess which makes being outside feel like a breeze.

Again, I don’t want to fool you, every year the chance of wildfires seems to increase, but still — summers are very pleasant by and large. But look at me go! Here I am telling you that summer is the best time to visit Portland but I’m not sharing my favorite activities.

Shame on me, let’s get to it! Here’s a roundup of my favorite summer activities in Portland.

Summer Activities | Best Time to Visit Portland

Visit the impressive Portland Rose Garden

Portland’s beloved rose garden is the largest and oldest rose garden in America. Home to an impressive 650+ varieties of roses and more than 10,000+ bushes, it’s easily one of the best free things to do in Portland. But the history of the rose garden is the best part, learn about it here.

Experience the Cathedral Park Jazz Festival

If you’re looking for fun things to do in Portland during the summer I highly recommend enjoying some listening talented jazz musicians at the annual Cathedral Park Jazz Festival, held every July over the span of a long weekend.

This popular festival is open to all ages and brings together a community of jazz lovers in an easy-going setting. Bring a picnic blanket or camping chairs and allow yourself to enjoy the pure bliss of music and nothing else. Learn more here.

Catch the epic swift migration at Chapman Elementary School

I often tell folks the best time to visit Portland is mid-September. The Labor Day crowds have left, the temperatures are mild, fall colors start coming in and the epic swift migration at Chapman Elementary School takes place.

Every September, like clockwork, the swifts at Chapman Elementary circle the iconic chimney (at sunset) before diving in for the night. It’s a spectacle to behold and one that draws in thousands of locals every year. Pack a picnic blanket, invite some friends and participate in one of the best activities in Portland. Learn more here.

The second best time to visit Portland is fall

Daily average temperatures: September (75°) | October (63°) | November (52°)

If you’re into gray skies and cozy cafes, you may find fall to be the best time to visit Portland. And you’d be right. Temperatures tend to dip lower day-by-day and heavy clouds creeping in. (I swear those clouds are determined to stay through spring!).

Early fall is a beautiful time to visit Portland because of the kaleidoscopic display of fall colors. Plus, the weather is pleasantly chilly and perfect for those that look good in bulky layers (unlike yours truly who risks getting offered a gig as the Michelin Man mascot at the local car shop).

If you’re visiting Portland during a particularly beautiful fall day, make your way out to Hood River for the Fruit Loop Drive. Bounce from our orchard to the next, in search of the best apples and baked goods in town (this is something you won’t want to miss!).

If the forecast guarantees blinding rain, know this: Portlanders have learned to thrive in gloomy weather. Our cozy cafes are nationally renowned and are breweries are worth pausing a diet over. There’s plenty of indoor activities to take advantage of on rainy days, but clear days are equally possible.

Getting a mix of typical Portland weather while still enjoying all the city has to offer is why why is one of the best times to visit Portland.

Fall Activities | Best Time to Visit Portland

Go to a pumpkin patch on Sauvie Island

Ah! If you were to ask me about the best time to visit Portland outside of summer, the answer would be too easy: Fall! Days filled with friends hopping from one pumpkin patch to the next (and taking proper breaks for spiked cider and beer, of course) it doesn’t get better than this.

Sauvie Island has a handful of prime pumpkin patches to choose from. Here’s a roundup of my favorite pumpkin patches near Portland.

Peruse the PSU Farmers Market

The PSU Farmers Market is the crown jewel of Portland’s renowned local cuisine scene (according to me). There’s nothing I love more than visiting a farmers market during the early weekend morning to snatch some goodies. Fall is one of the best times to visit Portland because of the great produce at arms reach (those apples from the Kiyokawa Farm stand!).

Stroll the market in search of some local seasonal delights and split a cozy homemade meal between generous pours of local wine. It’ll be an evening you won’t soon forget. Read more here.

Enjoy apple picking in Hood River

Yet another cozy fall tradition that proves fall is arguably the best time to visit Portland: Apple picking in Hood River. My husband and I have made this an annual tradition the past seven years. We invite some close friends to meet us at local orchard where we spend a couple hours before moseying to a relaxing winery.

Our friends enjoy this tradition so much they typically reach out in August to get it on the books. We’ve also noticed that all our friends return from one year to the next, which means our table at the winery grows year after year. Seems like nobody is willing to give up this tradition anytime soon and I can’t say I blame them.

Visiting Portland in Spring

Daily average temperatures: March (56°) | April (61°) | May (68°)

Spring is my husband’s favorite season but I don’t hold it against him — he’s not originally from Pacific Northwest. How could he possibly know that spring is marred by sideways rain and a necessity for rain boots? Like I said, not his fault.

We’ve had many friends ask if spring is a good time to visit Portland and the answer is typically a mixed bag. I typically encourage them to wait for summer (it’s pure bliss) but my husband says the rain isn’t as bad as people make it seem (and promptly darts a well-deserved look in my direction).

But the truth of it is this: you’ll be spending a lot of time indoors if you’re visiting Portland in spring. Between the chill and the rain, this is the perfect time to cozy up to a good book at a local cafe before driving over to a wine bar or brewery. Heck, start drafting that novel you’ve been putting off for years — the setting will be perfect!

Spring Activities | Best Time to Visit Portland

Portland Dining Month

There’s no denying that Portland is a foodie city through and through. Luckily, if you’re visiting Portland in March, you can see for yourself. Portland Dining Month is a highly-anticipated annual event wherein 100+ restaurants offer discounted three-course meals to those lucky enough to snag a reservation. I’ve discovered many new-to-me gems this way and can’t recommend it enough.

Experience the breathtaking cherry blossom season

If there’s one event that will bring out even the most home-bodied Portland introvert, it’d be the cherry blossoms at Tom McCall Waterfront. This is the best spot in Portland to see cherry blossoms during peak bloom. The 100 Akebono cherry trees that line the waterfront were gifted by the Japanese Grain Importers Association in 1990.

Visit the Wooden Shoe Tulip Festival

If you dream of frolicking through never-ending fields of tulips, I’m about to show you why you cannot afford to miss the ultimate tulip festival in Oregon — the Wooden Shoe Tulip Festival in Woodburn, Oregon.

To make the most of your visit, try to visit the Wooden Shoe Tulip Festival during peak bloom. Exact peak times vary from year to year, but, generally speaking – the first few weeks of April are a safe bet. Learn more here.

Experience the Portland Rose Festival

The Portland Rose Festival is the city’s pride and joy, and heck — they don’t call us the City of Roses for nothing. The Rose Festival is the 2nd largest floral parade in the country and locals eat it up! Held every year during the last weekend in May through the first two weeks of June, this is the biggest spectator event in the state.

Visiting Portland in Winter

Daily average temperatures: December (46°) | January (47°) | February (50°)

While talking about the best time to visit Portland, let’s also cover the worst time: winter. Yep, as a lifelong local, I can confirm that visiting Portland in winter may prove to be miserable.

The saving grace is the creative concoctions churning out of Portland’s best breweries. Check out the Holiday Ale Fest in Pioneer Courthouse Square to sample seasonal ales and sours, you’re bound to find memorable favorites.

If you’re visiting Portland in November, don’t miss the chance to see the annual tree lighting festival in Pioneer Courthouse Square the day after Thanksgiving. The square swells with locals and tourists alike, everyone eager to kick off the official start of the Christmas season.

Winter Activities | Best Time to Visit Portland

Check out the Holiday Ale Festival

Of all the things Portland is known for, perhaps the most notable is Portland’s beer scene. In fact, Portland is often rated as the best beer city in America. Our area of expertise? Craft beers and IPAs.

Swing by the Holiday Ale Festival (typically a weekend in early December) to sample more than 50 beers under the canopy of the decorated Christmas tree in Pioneer Courthouse Square. Learn more here.

Explore Powell’s Books

Rated by CNN as one of the coolest bookstores in the world, Powell’s Books, dubbed City of Books, is the largest independently owned bookstore in the world – selling both new and used titles for all to enjoy.

Home to more than one million new and used books, the store covers 4 floors. If that sounds overwhelming, grab a map before embarking on the adventure. Arrive early or be prepared for crowds, visiting Powell’s is by far one of the best things to do in Portland.

Fun fact: Pop into the Gold Room during your visit to see the rarest books in the store. The most expensive book at Powell’s is an 1814 copy of the Lewis & Clark Journal which includes Captain Lewis’ map safely tucked between the pages. The price? $350,000.

Get the BEST hot chocolate from Creo Chocolate

A little known local secret that I’ll let you in on: Creo Chocolate has the best hot chocolate in Portland. This ma and pa shop churns out rich, perfectly sweet and irresistibly satisfying hot chocolate .

I dream about it whenever I’m within 5 miles of downtown. Plus, the folks that own it couldn’t be sweeter (their their award winning chocolate bars).

Enjoy a meal at Le Pigeon

Oh my, what can I say about Le Pigeon that I haven’t said before. This restaurant is a dream — it put Portland on the culinary map! The award-wining restaurant offers tasting menus exclusivity and getting a last minute reservation may require donating a kidney (all the better, there will be more room for food).

It’s pricey but memorable (and filling), so it’s worth every penny. Don’t sleep on the wine pairing either — it’s top notch.

Check out the Portland Jazz Festival

The Portland Jazz Festival is a part of Black History Month celebrations. You can catch world renowned jazz musicians perform more than 150 concerts in Portland for two weeks in February. Learn more here.

List of Events in Portland by Month | Best Time to Visit Portland

Visiting Portland in January

• Fertile Ground Festival. This beloved Portland festival spans 11 days and hosts performing artists from all corners of the city. The festival is produced and hosted by the Portland Area Theater Alliance (PATA) and features live performances throughout the city. Everything from dance and theater to comedy and music.
• Note: Fertile Ground Festival will be on hiatus for 2023. I’ll update this with more info when available.

• Portland Old Time Music Gathering. As you may have guessed, this is a gathering of musicians specializing in old time music. Various bands serenade audiences at several venues around town. Learn more here.

Visiting Portland in February

• The Portland Jazz Festival is a part of Black History Month celebrations. You can catch world renowned jazz musicians perform more than 150 concerts in Portland for two weeks in February. Learn more here.

• Winter Light Festival. The holidays aren’t over until we say so, and we want them to linger until February. Experience a dazzling display of bright lights and matching musical shows on the epic Tilikum Crossing Bridge and along the Central Eastside. More details here.

• Zwickelmania. Held the second weekend in February, this beloved brew festival is all about celebrating Portland’s unwavering commitment to craft brews. Visitors can sample brews from local breweries in an attempt to stay warm from the elements. Each brewery offers something different, learn more here.

Visiting Portland in March

• Portland Dining Month. THIS highly-anticipated annual event wherein 100+ restaurants offer discounted three-course meals to those lucky enough to snag a reservation. I’ve discovered many new-to-me gems this way and can’t recommend it enough. Learn more here.

• Saint Patrick Festival. Locals count down the days until the lively four day celebration of St. Patrick’s Day with live music (bagpipes!), dancing and beer (lots and lots of beer). More information here.

• Portland International Film Festival. If you’re into indie movies, you’ll love this popular Portland festival. The event draws more than 35,000 visitors annually and premiers more than 100 international films. Info here.

• Shamrock Run. I’ve participated in the Shamrock Run many years and it’s such a blast! Tons of folks decked out in vibrant greens as they run the 5k, 8k or 15k route. The event is energizing and super fun. Live music, peppy performers and the glowing buzz of exercise, it doesn’t get better than this. Even if you don’t plan to run the route, join in on the sidelines, it’s a ton of fun. More information here.

Visiting Portland in April

• Cherry Blossoms at Tom McCall Waterfront Park. This is the best spot in Portland to see cherry blossoms during peak bloom. The 100 Akebono cherry trees that line the waterfront were gifted by the Japanese Grain Importers Association in 1990.

• Wooden Shoe Tulip Festival. If you dream of frolicking through never-ending fields of tulips, I’m about to show you why you cannot afford to miss the ultimate tulip festival in Oregon — the Wooden Shoe Tulip Festival in Woodburn, Oregon.

• To make the most of your visit, try to visit the Wooden Shoe Tulip Festival during peak bloom. Exact peak times vary from year to year, but, generally speaking – the first few weeks of April are a safe bet. Learn more here.

Visiting Portland in May

• The Portland Rose Festival. They don’t call us the City of Roses for nothing. The Rose Festival is the 2nd largest floral parade in the country and locals eat it up! Held every year during the last weekend in May through the first two weeks of June, this is the biggest spectator event in the state. Learn more here.

• Cinco de Mayo Festival. Experience the vibrancy of Mexican culture through music, food, crafts and dance. This 3-day even is held at Waterfront Park the weekend of May 5th, it’s hosted in collaboration with Guadalajara (Portland’s Sister City). Learn more here.

Visiting Portland in June

• Portland Pride. A week-long celebration of various events celebrating the beauty of the LGBTQ+ community. The star of the show is the Pride Parade hosted at Tom McCall Waterfront Park. Learn more here.

• Pedalpalooza. Portland is one of the best biking cities in the country, so it’s only fitting that we host one of the most fun biking events in the world. Thousands of bikers take off as streets are closed off to vehicle traffic. Learn more here.

Visiting Portland in July

• Oregon Brewer’s Festival. Founded in 1988, the Oregon Brewer’s Festival is hosted at Waterfront Park late-July. The park swells with visitors eager to get their hands on delicious beers from 90+ breweries. If that’s not enough to entice you, it’s the longest running craft beer festival in the country. Learn more here.

• Waterfront Blues Festival. Held during 4th of July weekend, head to the Waterfront Blues Festival at Tom McCall Waterfront Park. This is the second-largest blues festival in the country (second to Chicago) and attracts more than 120,000 people every year. You can catch more than 150 performances over the span of 4 days, learn more here.

• Cathedral Park Jazz Festival. If you’re looking for fun things to do in Portland during the summer I highly recommend enjoying some listening talented jazz musicians at the annual Cathedral Park Jazz Festival, held mid-July over the span of a long weekend.
• This popular festival is open to all ages and brings together a community of jazz lovers in an easy-going setting. Bring a picnic blanket or camping chairs and allow yourself to enjoy the pure bliss of music and nothing else. Learn more here.

Visiting Portland in August

• Providence Bridge Pedal. This is one of the best events in Portland. Grab your bike and pedal across iconic Portland bridges while they’re shut down to cars for one day of the year. Admission required and you’ll want to book early because this is a popular Portland event and sells out. Learn more here.

• Portland Beer Week. A 10-day celebration of local beer! You can probably tell by now that Portlanders love their beer and we’re not shy about it. Learn more here.

• Adult Soapbox Derby. Held at Mt. Tabor (one of the best parks in Portland) watch as participants zip down a dormant volcano on homemade derbies. It’s a sight for sore eyes, learn more here.

• Hood to Coast Relay. Ask any local about the Hood to Coast Relay and they’ll tell you they’ve either (a) checked it off or (b) have it on their radar. Spanning 198 miles, this is the longest relay race in the country and takes participants from Mount Hood to the Oregon Coast. More info here.

Visiting Portland in September

• Swift migration at Chapman Elementary. Every September, like clockwork, the swifts at Chapman Elementary circle the iconic chimney before diving in for the night. It’s a spectacle to behold and one that draws in thousands of locals every year. Pack a picnic blanket, invite some friends and participate in one of the best activities in Portland. Learn more here.

• Rose City Comic Con. If you’re into comics, you’ll love this Portland event held late September. This is a family-friendly celebration that focuses on comics, gaming, cosplay, sci-fi, anime and every fandom in between. More info here.

Visiting Portland in October

• Portland Marathon. Held the first weekend in October, the Portland Marathon is a very popular event that gets the whole city buzzing. Watch as athletes run around the city and cheer them on from the sidelines (unless you’re bold enough to join in!).

• Portland Fresh Hop Fest. Held at Oaks Amusement Park, this 2-day even celebrates fresh hop beers brewed by craft brewers in Oregon. Learn more here.

• FashionNXT. What’s next in fashion? Find out at FashionNXT, Portland’s eco-friendly spin on New York Fashion Week. Designers from all over the world show off their skills while keeping sustainability at the forefront. Learn more here.

Visiting Portland in November

• Portland Book Festival. Hosted at the Portland Art Museum, the Portland Book Festival is a celebration of bookworms! The even features author discussions, writing workshops, readings, kid’s story time and book fair. Swing by to see who’s up and coming, Portland is known for producing great authors!

• The Holiday Tree Lighting. This highly anticipated event occurs the day after thanksgiving. Watch in awe as the decorated 75-foot Douglas Fir in Pioneer Courthouse Square gets lit up for the first time! It’s the official start of the holiday season and it wouldn’t feel like Christmas without it.

Visiting Portland in December

• Swing by the Holiday Ale Festival (typically a weekend in early December) to sample more than 50 beers under the canopy of the decorated Christmas tree in Pioneer Courthouse Square. Learn more here.

• Santacon Portland. Put on your best Santa costume and join hordes of locals as they crawl from one pub to the next. It’s a very popular Portland event for a reason and you’re bound to have a great a time! Info here.

What’s the best time to travel to Portland, Oregon? (Post Summary)

In sum, the best time to visit Portland, Oregon is summer, hands down. The temperatures are relatively mild, the chance of rainfall is minimal and you’ll have ample opportunity to enjoy the great outdoors the city is known for.

• Summer
• Fall
• Spring
• Winter

Cheers!