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Courtesy Travel Portland, Jamies Francis

One of America’s pioneering hipster cities, Portland has a unique set of offerings—its metro area boasts 37,000 acres of green space and as the birthplace of culinary legend James Beard, unsurprisingly boasts an incredible foodie scene. The perfect long weekend destination, especially when combined with a visit to Oregon’s winelands in the Willamette Valley (pronounced wil-AAH-mit), Portland offers opportunities for outdoor adventure with a dynamic artisan community and ever-friendly locals.

Cheat Sheet

Lay of the Land

“Oregon is an inspiration. Whether you come to it, or are born to it, you become entranced by our state’s beauty, the opportunity she affords, and the independent spirit of her citizens.”
~Tom McCall

Portland’s easy-going nature is evident in its many nicknames, from Beervana to Stumptown and Bridge City. The west coast equivalent of such hipster-cool cities as Austin or Nashville, Portland is a place of eccentric locals, boutiques hawking locally made goods, bespoke coffee shops and abundant parkland.

Oregon’s largest city, Portland flourished in the 1830s, when settlers arriving at the end of the Oregon Trail formed a community here. The current city is divided in two by the Willamette River (pronounced wil-AAH-mit, to rhyme with dammit, as locals will correct you) and lies in the shadow of Mount Hood. Thanks to its proximity to the aforementioned natural wonders as well as the Columbia River Gorge and Pacific City, a beach destination on Oregon’s coast, Portland is a wonderful place to explore the great outdoors, while also getting a taste of city life.

With a population of just 600,000, Portland is deceptively large and has many different neighborhoods, all of which have their own distinct charm. The downtown area, which encompasses the West End and Pearl District, is filled with restaurants, shops and the best hotels, including the Sentinel, Nines and Ace Hotel. Visitors could spend a weekend exploring just this area, but those who want to experience some of the city’s best restaurants will want to venture out to additional neighborhoods. The Alberta Arts District is one of Portland’s creative hubs with co-op markets, gritty street art and some fun restaurants like Bollywood Theater. The Mississippi area is a great place to spend a half-day, thanks to its many shops and handful of excellent restaurants (don’t miss Paxton Gate or Sweedeedee).

When to Go

Portland experiences temperate weather year-round, with temperatures in the high 60s from May to June and between 40-50 degrees Fahrenheit in the winter months. July, August and September, when the city hosts a number of festivals, are particularly lovely. 

Getting There

Travelers visiting Portland fly into Portland International Airport (PDX), which is serviced by 17 airlines and even has its own food cart pod. The drive into the city takes about 20 minutes. 

Getting Around

Thanks to its compact city blocks (roughly half the size of those in most major US cities), downtown Portland is easily explored on foot. To explore beyond the immediate city center, it is recommended to take an Uber. Those who wish to bike should use BIKETOWN, Nike’s bike sharing program, which has over 100 stations throughout the city.

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Beyond… Portland

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