Portland

Bridge City, Stumptown, Beervana, or the City of Roses—Portland is as eclectic as its nicknames. The four distinct districts all tout a variation on the theme “Keep Portland Weird.” Southwest houses the downtown city core, a bustling blend of high-profile retail, culture, art, and entertainment. Southeast clings to the Willamette River on its gritty edge, softening into quaint neighborhoods offering all levels of lifestyle. North/Northeast, or “NoPo,” is an evolving, ethno-diverse tract of livability dotted with affordable, hip haunts and a cooler-than-thou attitude. Northwest is the upscale sustainability model anchored by the Pearl and slightly adrift from Uptown/23rd. Together these districts deliver a trendsetting cultural crossroad catering to over eight million visitors a year.

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Photo by Elena Kuchko/Unsplash

Overview

When’s the best time to go to Portland?

There’s a reason Portland boasts the highest concentration of craft brewers and distillers on the planet: the rain. Starting in late September, it is a close companion, lasting well into June. That shouldn’t stop you from planning a trip any time of year. Fall boasts colorful scenery and bountiful harvests from local growers. Winter snow is a novel inspiration for intellectual and physical pursuits. Rains relent somewhat in spring, giving way to warmer weather and lingering light. Summer is sensational, with dry, sunny days stretching into glorious evenings perfect for peddling your bike through a happy-hour haze and beyond.

How to get around Portland

Do the 12-mile jaunt from PDX International to downtown on MAX. The $2.50 train ride to the city center takes 40 minutes, providing a great introduction to Portland’s transit environment. The taxi ride takes half the time and runs $40. Amtrak and Greyhound make it easy for West Coasters to drop in.

Skip the car and go by bike, train, tram, streetcar, and bus. A bike gets you everywhere easily, unless you venture into the West Hills for a mile-long uphill slog to the famous Rose Garden. MAX trains are bike-friendly and can enhance your cycling range. You’ll need a car to get up to the mountains, out to wine country, over to the coast, or up the gorge. Some hotels now offer bikes as part of their room package. Bike rentals are plentiful and convenient.

Can’t miss things to do in Portland

Rain or shine, day or night, you can always make the pilgrimage to Powell’s Books. A visit to Powell’s is more than a trip to a bookstore; it’s a literary expedition. The actual need to buy a book is irrelevant. Powell’s is a small city with food, drinks, and entertainment. Oh, and books—rows upon rows of books. The clientele is a cross section of PDX culture, from grandmas to hipsters, students to survivalists. Explore the color-coded rooms to your heart’s content, and then try to find your way out…

Food and drink to try in Portland

Dining in Portland is a remarkably delicious adventure. The fare is focused, local, and sustainably mouthwatering. Start with locally roasted morning coffee. Grab your gluten-free-for-all donut in the food cart pods. Mix up regional and international offerings between lunch and dinner. Do your homework on the food scene and come hungry. But don’t forget to let the spirit move you. With breweries, wineries, and distilleries littering the landscape, it’s easy to find something you’ll absolutely love. PDX turns happy hour into a lifestyle, so carve out that 4-7pm slot on the schedule to make the rounds.

Culture in Portland

Portland’s large reader population enjoys a library and a bookstore that each cover an entire city block. The city is a rich new-media outpost—with film, literature, art, and music spanning the cultural spectrum in a variety of venues and installations. The museum scene offers a full complement of content from art to history, science to forestry, all easily accessible and striving to give visitors context for their NW experience. Note that Portlandia (not the TV show) is the second-largest bronze statue in the United States, eclipsed only by the one on Liberty Island. See it!

Summer serves up some of the most entertaining events on the festival calendar. Cinco de Mayo kicks off the season; then the Rose Festival officially welcomes summer in June. The Waterfront Blues Fest fuels a carefree, all-ages party well into the evening on the Fourth of July, attracting national headliners. The Oregon Brewers Fest puts the beer in Beervana with summer and winter events. Go international with the Chinese, Polish, Italian, Greek, and German festivals. Music/Techfest NW is Portland’s all-out SXSW knockoff in fall. Portland International Film Fest lights up screens in winter. Bottom line—the party’s always pumping.

Practical Information

It’s all about the environment, so always bring rain gear. Pack jacket and pants if you’re planning on going native. Summer can be hot. Winter can bring snow. Fall and spring weather are all over the map, so wear your layers for a comfortable stay. Don’t forget your running, yoga, or exercise wear, and get a workout in. Major-league soccer with the Portland Timbers is a real treat, but tickets are tight, so plan ahead and sit with the “Timbers Army.” Across the river, Winterhawks and Blazers seats are more accessible.

Guide Editor

Jay Rymeski is a veteran writer, producer, and journalist based in Portland, Oregon.

READ BEFORE YOU GO
HOTELS
We’re living in the golden age of hotels that have craft cocktails, Instagram-ready design, and in-room turntables. These properties, ranging from West Texan motels to loft-like boutiques in the middle of city noise, are our absolute favorites of the breed.
RESOURCES TO HELP PLAN YOUR TRIP
This is where everyone stops to smell the roses in the Rose City. Celebrating its centennial in 2017, the International Rose Test Garden is the nation’s oldest continually operating rose test garden (where varieties are evaluated for characteristics such as disease resistance, bloom size, and fragrance). Originally conceived as a way to preserve different varieties of European roses from the destruction of World War I, the garden today contains 10,000 plants across 4.5 acres in Washington Park. Best of all, it’s completely free, whether you want to compare green thumbs with professionals or take in the views of Mount Hood while breathing in the perfumed air.
You can take your rented bike and pedal down to a waiting Zipcar and get out of town. From the mountains to the coast—and everything in between—you’ll enjoy an easy break from the urban outlook, usually with an hour of driving, or less.
No matter your passion, Portland has you covered. The tax-free shopping wonderland is loaded with stores to tickle the fancy of shoppers both casual and obsessed. From Powell’s City of Books—easily one of the best bookstores in the United States—to Wildfang, where the coolest patriarchy smashers hang, and, yes, all the chain stores, Portland’s got the goods. Some of the city’s shopping hubs include downtown Portland, Pioneer Place, 23rd Avenue, and the Pearl District. Fuel up with some java at the coffee shop of your choice because there is serious shopping to be done.
Portland has long been one of America’s culinary “it” cities and that won’t change anytime soon. The city’s cooks do so many things so very well: from doughnuts to dishes that focus on seasonal and locally-sourced ingredients. Eat around the world without leaving the city limits with visits to the legendary food cart scene as well as top spots like Ava Gene’s, Kachka, and Hat Yai (their Thai fried chicken will make you want to move to Portland). Pull up to one of these restaurant tables and you’ll find yourself challenged and delighted and definitely eager for more.
Whether you’re searching for a caffeine boost to kick off a day in Portland or you’re on the hunt for a perfect place to perch for some people watching, the city’s cafe scene offers plenty of options. From drip coffee to espresso drinks at third wave coffee roasters to donut spots and bakeries that also serve up good java, your time in Portland is about to get turbocharged. Don’t forget to pick up some to-go beans from local coffee roasters. You’ll want to brew up some of Portland’s coffee scene long after your visit.
Readers are escaping into fiction during the coronavirus pandemic.
With a new luxury hotel, a promising restaurant scene, and loads of outdoor adventure, this jewel of the high desert makes for the ideal escape from the City of Roses.
Wine lovers, rejoice: the French-style bar à vins, beloved especially in Paris as a casual, personality-driven neighborhood haunt for regular wine drinking, is staking a claim in the United States.
Sometimes you just want get back to the basic. Pizza. Beer. More Pizza. Look for the giant slice on the side of the building. You’ll find the place no matter what state of mind you’re in. Sizzle Pie is perfectly positioned to help get that hunger monkey off your back. It’s centrally located in Downtown, sells by the NY-sized slice, and tastes extra extra good at 2 AM.

Don’t ask why. It just does. #Believe

Let’s be real here. You’re in Portland. You’ll be up late. Just don’t forget that Sizzle Pie’s got your back...or maybe the monkey does…

A leader in Portland’s vegetable-forward movement, Quaintrelle has quietly become one of the city’s best fine-dining choices. All this on a strip of Mississippi Street better known for bar crawls and brunch lines than for seasonal cuisine and killer cocktails. The eclectic American menu rotates based on what’s available and in season. Almost all of the food is local, from the tempura Meyer lemons to the carrot and raisin salad. Meals at Quaintrelle can easily double as a primer on what can be grown in Oregon, including wouldn’t-guess-this-is-local ingredients like quinoa and wasabi.