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.


Photo Courtesy of Josemaria Toscano


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 Portland, Oregon Local Expert

Jay Rymeski is a veteran writer, producer, and journalist based in Portland, Ore. With master interview skills and storytelling at his core, Jay continues building a career contributing to organizations like NBC, ABC, Nike, Anheuser-Busch, and Mercy Corps. His domestic and international lifestyle and cultural writing has a dedicated online following. He is an accomplished runner, mountaineer, kayaker, and telemark skier with a passion for adventure. You can delve into more data on him at currentcom.

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