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
Doughnuts are to Portland what coffee is to David Lynch, both essential fuel and calling card. While there are many pretenders to the title of the city’s best doughnuts—Voodoo Doughnuts certainly sells the most Instagrammable food products—Blue Star, from ubiquitous local restaurateur Micah Camden, is the most consistent. Flavors range from powdered sugar to maple bacon to passion fruit cocoa nibs, sold fresh daily until no more remain. The downtown location gets crowded early on weekends, so plan ahead. In a pinch, grab them at Blue Star’s airport location—which makes asking a friend to pick you up at the airport a sweet request indeed.
The Tin Shed is probably nowhere near wherever you might be in Portland but that matters not. Get a cab and go over there because the biscuits are so good they’ll make you wanna slap yo mama! You serve yourself coffee while you wait under the covered patio seating, they welcome dogs and their bloody mary is spectacular. This place rocks. Go check it out.
Right around the corner from Powell’s Bookstore and Sizzle Pie, the vibe here is fantastic. The walls are kind of spartan, there’s a record player in the corner, and you can roam on free Internet to your heart’s content. These guys definitely know the food scene here and have great tips. My iced chai latte? Served in a mason jar. Yum and Yum. And those caneles, pictured? They were featured in Portland Monthly. I believe Courier is following the ice cube trend with one big block of ice in either a square or rectangle. I also love the everyday musings on their blog.
This is one of the new hot bars, just a few blocks down from the Jupiter Hotel on SE Grand and Morrision. Checkpoints: skinny hot bartenders in wifebeaters who shake up some inventive cocktails, a DJ, a 110-year old piano, a horseshoe bar and an impressive late night menu (cuban sandwiches, anyone?). I had the Sam Issacs which was mentioned in Portland Monthly as the drink to have but not even on their menu. It has bourbon, mint, blackberries and lime. It’s DELICIOUS. Portland seems to have a thing for libations with ginger beer and I’m loving it. I followed up with 96 Tears, a combination of vodka, lime, ginger and ginger beer. This was light but boozy. The perfect way to start a night or in this case, I’d end it here if you want to dance.
The tram gives Portland visitors stunning views of the city, river, and mountains beyond. Grab the streetcar from downtown out to the waterfront. You’re delivered to the lower terminal for the three-minute ride carrying you 3,300 feet at 20 MPH to the upper terminal at OHSU. Linger for photo ops then head back down to explore. If it’s nice, skip the streetcar and walk back along the river. Daily workout, check. Roundtrip cost: $4. At the lower terminal, the Daily Cafe is an easy find in the atrium of the OHSU Clinical building as you disembark the pill-shaped car, built with precision by the Swiss. Head for the river and stroll along the shore in any weather. Double back along SW Bond Ave and consider lunch at Bambuza Vietnamese Bistro. Check out the pricey high-rise condos on the market in the real estate office windows, then relax in one of the pocket parks to people watch. It snows in Portland. A couple of times a winter, even downtown gets dusted and it’s a huge mess. I’ve dreamed about getting my ski gear on, grabbing my boards and heading for the PDX Tram at the South Waterfront. I’d casually climb aboard with the patients and medical folks heading up to “Pill Hill” and blow their minds.
I wouldn’t normally visit a hotel restaurant just for the purpose of having a sandwich. But this is the second restaurant by Vitaly Paley, one of Portland‘s most beloved chefs, and I’d been told it was a good place for lunch. I hadn’t guessed that most of the menu would be sandwiches, and I have to admit to feeling a little disappointment when I saw it. I shouldn’t have. The dungeness crab reuben was a flaky fish marvel, while the heirloom tomato salad I had with it was a perfectly pert accompaniment. The homemade cream soda, meanwhile, was as sweet and delicious as anything in an Enid Blyton novel, and it had me suppressing the urge to exclaim “How jolly!” Anyway. That’s just me. If you like a sandwich, I think you’ll probably like these.
I was on a cruise in Italy when I heard about this place. I’d mentioned that I was heading to Portland, and a fellow cruiser, a native of the town, had told me that if they had one recommendation it would be the ice cream at Salt and Straw.

What she didn’t tell me was that the flavors are not your usual vanilla, chocolate, and raspberry ripple. In fact, the first thing I tasted at Salt and Straw was their new “Bollywood” recipe, which included carrot custard and cardamom, which sounds almost sensible when you considered that some of their most popular flavors include prosciutto and goat cheese.

There was a huge line, even on a Friday mid-afternoon, but it was worth it for the almond brittle with salted ganache, not to mention the apple pie with real chunks of cheddar cheese. They’re doing their best to “Keep Portland Weird” here...and it tastes good.
The Portland Art Museum has been a fixture of the Rose City for longer than you’d expect—it’s the oldest art museum on the West Coast, opened in 1892. The current location, on the South Park Blocks, debuted in 1932 with a design by Pietro Belluschi. Today, the permanent collection includes 42,000 works along with a rotating selection of exhibits. Among the highlights in past years: pieces by Rodin and Andy Warhol, and what is thought to be the largest cat painting in the world. The 2.5-block campus also includes the Northwest Film Center.
When traveling, I love to spend Saturday morning at the farmers market. There’s no better way to meet the locals and get to know the town culture. What produce do they love? What coffee do they sip? What’s the overall mood? One of the best Saturday morning farmers markets I’ve been to was in a giant park in Portland, Maine. The stalls were packed with reasonably priced, locally grown produce (of course, Maine blueberries were abundant). Despite the chilly morning temperatures, children played in a splash park and adults sipped locally made apple cider while listening to the various jazz musicians who had set up around the farmers market. Despite the crowds, parking was abundant (such a rarity!) as was the “Maine nice” that we found around the entire state.
An iconic name in Portland retail—as well as among readers who have never been to the city—Powell’s has multiple locations on both sides of the Willamette. The downtown store remains the one best suited for visitors to explore, with miles of used reads, a tightly curated selection of books from the knowledgeable staff, and every Portland-themed book you could hope to find under one roof. A renovation in 2014 opened up the space and made it feel less like a warehouse of dusty stacks, an improvement that bodes well for the future of the business. Author appearances, even those at the satellite branches, are some of Portland’s best events for interesting discussions.