I was so excited to be in Portland as part of an exciting campaign with Booking.com and Time Out New York sharing a spontaneous “last-minute” weekend getaway in Portland! I’d always wanted to “wing it” and head to a random destination without planning a thing.
My weekend consisted of the "best of" Portland: farm-to-table food, craft beer from local breweries and even a day swimming in waterfalls! As a San Diego native, this really opened my eyes to just how close adventure can be and that booking a last-minute adventure is just a click away on Booking.com.
The top 10 things to do in Portland
The largest new and used bookstore in the world, Powell’s City of Books is home to more than a million new, used and rare tomes. It’s so large, in fact, that customers are given color-coded maps to prevent them getting lost in its labyrinthine floors. In the Purple Room, check out the Espresso Book Machine, which you can use to publish your own book in the time it takes to make a cup of coffee. The Rare Book Room has plenty of signed volumes if you’re hunting for a one-of-a-kind gift, and look out for big-name author events in the art gallery upstairs.
From bacon and maple syrup to bubble gum, the doughnut menu at Voodoo looks more like Willy Wonka’s to-do list. Most of these flavors shouldn’t work. But somehow they do—incredibly well. Voodoo Doughnut now has six locations, but aficionados head to the much-loved original store on Portland’s SW Third Avenue for their sugar fix. If it’s your first time, go for the classic Voodoo Doll, a chocolate-covered confection shaped like said effigy and packed with red jelly. Or if you’re feeling confident (and hungry), try the infamous Tex-Ass Challenge doughnut. It’s six times larger than normal—but if you can finish it in 80 seconds, you’ll get your money back.
The best way to explore Portland is on two wheels. Local operators Pedal Bike Tours and Portland Bicycle Tours offer great guided options within the Rose City and out into the surrounding countryside (Pedal Bike Tours’ guided ride to the lush Columbia River Gorge is particularly beautiful). Both companies run food- and drink-centric tours—including one in which you pedal between the city’s best microbreweries, building up a suitable thirst en route—but if you don’t see one you like, they can create a customized themed ride.
Cup and Bar caters to two of our favorite vices: locally roasted coffee and bean-to-bar chocolate. The confectioner-cum-roastery opened in March 2015 and is already one of the most popular spots in town. A collaboration between local companies Trailhead Coffee and Ranger Chocolate, it sells all kinds of delicious handmade treats from its quirky premises in the old Stark Vacuum Warehouse—all ethically sourced, of course.
Portland is rightly famous for its craft beer scene, but fans of the hard stuff now have their own clubhouse here too. The Multnomah Whiskey Library stocks an incredible selection of more than 1,000 bottles of the liquor from around the world, all in a beautiful bar that exudes sophistication and old-school class. It’s already one of the finest whiskey bars in the world, but that’s just the start. An additional bar, the Green Room, just opened downstairs with a focus on beer, wine and cider. If all libraries were like this,we’d be a lot more studious.
From brewing and baking to carving and welding, Portland is known for its DIY culture. Among the art galleries, shops and restaurants in the thriving Pearl District, the new Made Here PDX on NW 10th Avenue is the biggest and best showcase of handmade wares. A cross between a gallery and a street market, it sells everything from skillets and small-batch hot sauce to denim jackets and kayaks.
People drive in from Seattle and beyond to eat at Pok Pok, the Thai restaurant from popular homegrown chef (and former DJ) Andy Ricker. Almost a decade since opening, the SE Division Street eatery is still one of the hottest meal tickets in town (and a lot of fun), so expect a line. Order the outstanding laap meuang (northern Thai minced pork salad), with a side helping of the phenomenal Vietnamese fish-sauce wings, which have become something of a social media sensation in their own right. The portions can be small, but that’s just a good excuse to order more of them.
Portlanders have been going back to school in droves—namely, George Washington High School, which reopened as live music venue Revolution Hall in early 2015 and has since counted Neko Case and Soul Asylum among its headliners. The iconic 113,500-square-foot brick landmark on SE Stark Street has been extensively renovated, and additions include a popular rooftop bar with outstanding views across the city. It sure beats sneaking a beer behind the cafeteria.
This French Renaissance–style château perched high in the West Hills was originally built for The Oregonian’s wealthy publisher Henry Pittock in 1909, and purchased by the city in 1964. It’s now a museum, telling the story of Portland’s growth throughout the last century, through the eyes (and belongings) of the prominent Pittock family. At more than 1,000 feet above sea level, Pittock Mansion commands some of the finest views over the city, making its lawns a popular picnic spot.
In recent years a number of Willamette Valley vintners have shifted their operations from wine country into downtown Portland. There are now more than 10 wineries, complete with tasting rooms, within Portland’s city limits, forming an unofficial urban wine trail. If you don’t have the stamina to hit them all, prioritize Southeast Wine Collective (2425 SE 35th Pl; 503-208-2061), a collaboration of some of the better small wineries under one roof, or head to Clay Pigeon Winery (815 SE Oak St; 503-206-8117), where on-site wine bar, Cyril’s, serves delicious cheese boards, burgers and other snacks to offset your vino consumption.
Top-rated hotels on Booking.com
In case you couldn’t tell from the name, this 782-room complex is all business: it sits just a block from public transportation on the MAX, and offers a ballroom along with 16,000 square feet of event space, plus two restaurants (a gastro pub and northern Italian grill) and complimentary access to two fitness centers and two indoor pools. Sleeping quarters are inoffensive and modern—in the Executive tower (the hotel is split between two buildings), rooms and suites benefit from more space and upscale amenities like minifridges, Keurig coffeemakers and L-shaped desks.
Property-wide free Wi-Fi, nightly wine hours and “companion” goldfish bowls (to relieve loneliness—yes, really) have endeared Kimpton to the hearts of many a traveler, but this iconic property, opened in 2007, hits a special note. It’s housed in a National Register of Historic Places-listed former 1912 department store, and the quirky rooms reflect that history with richly upholstered furnishings, framed mirrors and vintage-inspired wallpaper (in addition, of course, to Frette linens, 32-inch flat-screens and minibars). Organic coffee is poured each morning in the lobby, and the contemporary American eatery—known for its extensive whiskey library—offers 24-hour room service.
Unlike its colorful sister property downtown, this Kimpton hotel channels rural Oregon with its front-row river views, abundant outdoor spaces and chalet-style lobby with a stone fireplace. Earthy, den-like rooms come with all the trimmings, while some suites even feature wood-burning fireplaces and kitchens; for longer stays, there’s a separate annex with condo units overlooking the marina. At Three Degrees, the hotel’s laid-back seafood grill, pull up a rocking chair on the heated, year-round porch, or settle inside for fresh oysters and Alaskan scallop crudo.
No, you’re not coming here for the Michelin-starred dining or the decor, but you could do worse than holing up at this cookie-cutter chain for a few nights. Set back from the Columbia River, it offers free shuttle service to the airport, which sits just 2.5 miles away, any time of the day or night. The rate also gets you free Wi-Fi, hot breakfast and access to the on-site gym and indoor pool. Need to heat up a can of SpaghettiOs for a quick pre-flight dinner? In-room microwaves and coffeemakers make eating on the fly a cinch.
Hostels are rarely short on personality, and this cozy, three-story Portland manse is no exception. The structure dates back to 1889—complete with a deck and a furnished patio—yet thanks to owner Jim Kennett’s intuitive touch, the rooms (both dorm-style and private) feel airy and bright, rather than antiquated. In line with its free-spirited clientele, the front desk remains open 24 hours, and there are bike rentals, free Wi-Fi and frequent organized activities like group dinners and pub crawls to keep travelers engaged.
Making a last-minute pit stop on your road trip? Friend’s couch didn’t work out? Best Western is always a safe bet. With a grand lobby hall and a U-shaped layout that encloses an outdoor pool, hot tub and sundeck (perfect for catching a few rays, when the weather permits), the property is more resort-ish than you might otherwise expect—free cooked breakfasts are also a nice perk. Rooms are fully modern; we recommend requesting a private terrace or balcony overlooking the pool courtyard, otherwise you might end up facing I-205 across the street.
Within the Intercontinental Hotel Group (of which Staybridge Suites is a part), there’s a chain to suit practically every taste. This one’s for budget travelers who like built-in comforts while they’re on the road. If you have pressing work, there’s free Wi-Fi in all rooms, plus a cushy business center; if you’re catching a flight, a free airport shuttle runs 21 hours a day; if you’ve just come back from the Portland Farmers Market, there’s a full kitchen with a stove, cookware and a dishwasher in every room. Not to mention the 24-hour gym and heated indoor pool. Who needs Four Seasons, anyway?
If the idea of sleeping above a Macy’s seems tacky to you, consider that in 1909, when this 15-story building went up, department stores were upper-tier barometers of culture, offering exclusive glimpses into the latest designs, fashions and technology. In 2008, an $18 million renovation converted the top floors of this glazed terra cotta landmark into a luxury hotel, with a world-class contemporary art collection and regal rooms. But it’s the public spaces where this place really shines—take the light-filled atrium, which spans four floors and includes a library whiskey bar with a pool table and leather sofas. Departure, one of the hotel’s two eateries, serves upscale sushi on two rooftop patios overlooking the Willamette River.
In today’s celebrity-obsessed culture, a little old-school glamor goes a long way. Hotel deLuxe models itself after 1930s-era Hollywood—the vintage photographs of pouting starlets that decorate its plush lobby appear throughout the entire hotel, and there’s even a discreet cocktail bar called the Driftwood Room with a single curved bar and noir vibe that could be straight out of a David Lynch movie. Playing up the diva appeal, guests can indulge their wildest rooms service needs with a “Make It So” button on each telephone, and there’s even a Marlene Dietrich suite with an eight-foot circular bed.
As the hospitality trend moves toward ever tinier and more bespoke spaces, a classic mid-range tower like the Paramount can be refreshing. The down-to-earth property does just what it says on the box: warm interiors, spacious bathrooms with Gilchrist & Soames toiletries, and high-tech touches like free Wi-Fi, 37-inch HDTVs and MP3 clock radios—there’s even a tier of rooms and suites with chic French doors opening onto balconies with wrought-iron furniture. And for meals, there’s Swank, a bistro with rustic wood interiors, and a modern whiskey bar called Swine showcasing local spirits.