When you should visit Portland, Oregon

People who love Portland, Oregon will tell you to embrace the rain.

A reliable condition in the city from October to June, the rain is what makes the city so green, coating the trees and sidewalks in moss – and it’s why flowers bloom here nearly year-round. A good rain jacket and waterproof walking shoes are all you need to make the most of a rainy day. And when the sun finally comes out, the city sparkles. 

So should you visit for the rain or sun? At any time, you’ll find cozy coffee shops and cocktail bars, endless culinary delights, muddy or dry trails shaded by thick evergreen trees, and neighborhoods bursting with personality. Elements of every season in Portland contribute to the city’s moody vibe and vibrant personality. So whichever season you pick, you’ll likely want to make a return visit during another. 

Catch a rainbow of blooms from March to May 

While you’ll see blooming flowers at surprising times of the year in Portland, mid-March marks the most dramatic explosion of colors – namely, when the city’s beloved cherry trees come to life. The most famous and dramatic stretch of these blossoms is in downtown Portland, along the Willamette River, where the pedestrian path suddenly and briefly gets draped in heavy, pink branches. But these aren’t the only showstoppers in town. 

Visit Washington Park’s Japanese Garden for another popular yet serene cherry-tree tableau. Thanks to Portland’s close ties with its sister city, Sapporo, and a stunning 2017 expansion by world-renowned architect Kengo Kuma, this garden is a true homage to Japanese culture. Washington Park is also home to Portland’s famous International Rose Test Garden, which starts budding in April. (The bushes fully bloom come June.)

Crystal Springs Rhododendron Garden in Southeast Portland is a lesser-known but delightful place for bloom-spotting, with nine acres’ worth of rare species of rhododendrons and azaleas. These hearty shrubs can open as early as February, and peak in late April. Hoyt Arboretum also sees springtime blooms.

Portland’s beloved donut shops deliver equally colorful results. An iconic pink box of Voodoo Donuts will add another pop of color to your snaps of the cherry blossoms. Donut connoisseurs will point you to other shops that focus on freshly baked and perfectly flavored fried pastries, like Pip’s Original Doughnuts and Chai, Blue Star and Coco Donuts. 

The Portland Rose Festival serves as the unofficial kickoff to summer. The festivities comprise some 60 events starting in late May, including dragon-boat races, carnival rides, concerts, art shows and parades, including the iconic Grand Floral Parade through Portland’s Central Eastside.  

June to September is best for hiking and outdoor dining 

Summer in Portland is a smorgasbord of color and activity, which takes place on peaceful hiking trails, in verdant parks and all over lively city streets. After an inevitably long, wet spring, people are ready to be outside. 

Prepare for crowds in this peak tourist season. Patios fill up fast. Lines form for favorite summer spots like Salt & Straw ice cream. And parking lots overflow at entrances to Forest Park, the largest wooded urban park in the country, where you can hike on over 80 miles (129km) of trails. 

There are countless chances to enjoy nature on long walks in the city, including the short ascent up Mt Tabor, the city’s dormant cinder cone. Take the stairs to the top for a sweeping view of the city, then wander down Hawthorne Blvd, where you’ll find plentiful dive bars with patios, including the delightfully tacky Space Room Lounge. 

Farther to the southeast, head to Powell Butte Nature Park for gently rolling hiking trails and views of the many mountains that surround Portland, including Mt Hood, Mt St Helens and Mt Adams. Tryon Creek State Natural Area on the edge of southwest Portland is home to 665 acres of forest, 14 miles (22.5km) of hiking trails and 3 miles (5km) of paved bike trails. 

For post-hike refueling, the main Southeast thoroughfares of Belmont, Hawthorne and Division brim with food trucks, picnic tables, breweries and patios for enjoying Portland’s local fare alfresco. In the northeast, head to Alberta or Mississippi for more concentrations of food, drink and outdoor seating to enjoy. Or you can always get something to-go and head to Laurelhurst Park with a blanket for a meal among the massive Douglas fir trees.  

September to October is spooky season 

Portland loves Halloween, and appreciation for spooky season starts as soon as schools return from summer break. At Topaz Farm on Sauvie Island, just north of Portland, you’ll find copious pumpkins, a corn maze and a great selection of food and drinks that can be enjoyed while chickens run around your feet. 

Portland’s “weird” side is on full display at the annual West Coast Giant Pumpkin Regatta in Tualatin, just southwest of the city. Expect costumed paddlers navigating – yes – giant pumpkins in a series of races, while onlookers enjoy food and additional entertainment. 

These months are also a great time to check out Portland’s independent movie theaters, like the historic Hollywood and Bagdad – both stunningly ornate spaces where you can order local beer and food to enjoy during a flick. 

Embrace the dark with books and holiday lights in November and December 

Portlanders love their books – especially in the wintertime when the drizzly darkness sets the mood for curling up with a great read. If you’re looking to stock up, the world-famous Powell’s City of Books is a go-to any time of year. In November, the Portland Book Fest brings the stories off the page with author talks, lectures and classes. 

The darkness also sets the stage for lights. Visit the Oregon Zoo in December for ZooLights, a dazzling display of holiday sparkle. This event is especially popular with families; kids love to visit the animals as they marvel at the millions of lights on display all over the zoo grounds. 

February is craft beer time 

No matter when or where you’re exploring Portland, you can expect access to the country’s most famous beer scene, with some 80 craft breweries within the city limits. Come February, the beer enthusiasm gets turned up a notch with the arrival of Oregon Craft Beer Month. Breweries across the state host special events and release new batches – and for one February weekend, beer lovers can join in the nerdiest of events, at Zwickelmania, when breweries across Portland open their doors on this day for behind-the-scenes tours and brewer talks. Since Zwickel is German for the tap on the fermentation vessel that lets brewers taste their works in progress, you might even catch some free samples straight from the vat.