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  • For cross-country skiers, one winter destination rises above the rest: humble Hayward, Wisconsin, where, for a glorious weekend, their obscure sport is king.
  • The City of Roses is home to some of the most unique hotels in the Pacific Northwest, from a tiny house and converted school to a hipster favorite and elegant grande dame, the options are varied in both style and price. But other wonderful places to stay can be found throughout the Pacific Northwest state.
  • 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.
  • 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.
  • 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.
  • 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.
  • One month in Jamaica could mean four weeks of endless adventures, from beaches to museums and parties to festivals. Travel from lively Negril to lush Portland via Jamaica’s scenic north coast and fishing villages, before kicking back on the calm black sands of the south. The great thing about spending a whole month in Jamaica is that you have plenty of time to lounge on the beaches and to explore inland, so you get the best of all worlds.
  • 422 SW Broadway, Portland, OR 97205, USA
    Sure, the Hotel Vintage is classic (it was built in 1894 as the Hotel Imperial, one of Portland’s most iconic grande dames, and is listed on the National Register of Historic Places), but its name references another kind of vintage: the many renowned wines of the surrounding Willamette Valley. When the hotel reopened in 2015 after an extensive renovation, it announced partnerships with 117 local wineries (one for each guestroom), each of which sends a representative at least once a quarter to pour at the guest-only wine hour held every evening. Rooms feature original artwork made from recycled corks, and the trendy lobby bar (named for Bacchus, the god of wine) and local landmark of a restaurant offer an impressive list of some of the best local and Italian wines.

    Even those who don’t share the hotel’s passion for vino will find plenty to love, from the famously superlative Kimpton service to the private outdoor hot tubs and custom Public bicycles available to borrow. Also on-site is a game room—an extension of the lobby bar where guests and in-the-know locals mingle over retro video game consoles (Atari, anyone?), shuffleboard, and pool. We’ll raise a glass to that.
  • 1001 SW Broadway, Portland, OR 97205, USA
    Don’t let Portland’s low-key, outdoorsy-hipster vibe fool you: the Heathman Hotel is as grown-up and refined as they come. Opened in 1927 as an expansion of one of the city’s grande dame hotels, the Heathman continues to set the standard for classic luxury in the City of Roses. Rather than rest on its laurels, though, the hotel has consistently upped the ante, collecting a museum-worthy array of modern art (including a handful of Warhols alongside works by acclaimed local artists), boasting one of the most impressive collections of autographed books in the world, and offering guests a choice of mattress in the sumptuous rooms. Indeed, so famously decadent and romantic is the Heathman, with its award-winning restaurant and almost-nightly live jazz in the bar, that it was used as the setting for several of the rendezvous in E.L. James’ infamous Fifty Shades of Grey—although, for most guests, the original crystal chandeliers and marble fireplaces inspire magic enough.
  • 53000 East Historic Columbia River Hwy, Corbett, OR 97019, USA
    It was touch-and-go at moments, but 2017’s wildfires spared the lodge at this iconic waterfall in the Columbia Gorge, 30 miles east of downtown Portland. The stone structure at the site of the 620-foot, two-step falls was built in 1925, ten years after Multnomah Falls Park was dedicated. It’s an easy, paved hike up to the Benson Footbridge, situated between the upper and lower falls. On weekends and in the summertime, traffic can be a bear, so plan accordingly, either by arriving early or by taking advantage of the Gorge Express bus service, which departs regularly from the Gateway Transit Center in Portland.
  • 525 Rainier Ave S, Seattle, WA 98144, USA
    It sounds like a Portlandia sketch: the Northwest pizza joint with an on-site chicken coop, where you can get any pie topped with a soft-cooked egg. But Humble Pie is quite serious about their pizza (and their chickens); their goal is balancing Asian and Pacific Northwest architectural elements with sustainable urban farming. That means sunny wooden picnic benches right next to the outdoor coop, and sharing a table with new friends during their busy happy hour. The menu is heavy on local and organic ingredients, including the beer and cider selection. Our favorite was the pulled pork, pickled onion, and Beecher’s mozzarella cheese pizza — with an egg on top, of course.
  • 119 Exchange St, Portland, ME 04101, USA
    Hyperlocalism has fueled Portland’s Old Port District revitalization, with buzzy restaurants and shops with a deep sense of place opening in recent years. The stylish Press Hotel is no exception. A publishing motif runs throughout the 110-room property, which occupies a corner building that once housed the Portland Press Herald. Custom-made wallpaper printed with old headlines adorns the corridors, and desks inspired by those found in 1920s newsrooms are in each room. Works by local artists—including a dramatic installation of vintage typewriters from the late 19th and early 20th centuries by Portland artist Erin Hutton—and woven-wall tapestries by Portland home-goods designer Angela Adams also abound. (There are even a few notable—and welcome—nods to the global luxury market, including Frette linens from Italy atop the plush beds.) The focus at the 65-seat hotel restaurant, Union, is proudly farm- and sea-to-table, with dishes like house-smoked local mussels served with celery cream.
  • 1005 W Burnside St, Portland, OR 97209, USA
    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.
  • 525 SW Morrison St, Portland, OR 97204, USA
    Portland isn’t exactly the kind of city that’s known for being “fancy,” which was why it was so bold for the Starwood Luxury Collection to add a sleek 15th floor to the top of the iconic Meier & Frank department store building downtown—and turn the top nine floors into the swankiest hotel in town. Who would’ve thought that Louis XVI chairs, tufted white leather and teal velvet, crystal chandeliers, and ornate wallpaper would work so well in the city of plaid, beards, and twee bird patterns? In true Field of Dreams fashion, Starwood built it and the travelers came out of the woodwork, hungry for a luxury hotel that embodies the Rose City with everything from environmentally conscious practices and farm-to-table restaurants to an extensive art collection and rooftop honey bee colony. All that’s to say nothing of the private club-like Library, a collaboration with Portland icon Powell’s Books (the world’s largest bookstore) that allows hotel guests to borrow from a curated collection of 3,000 books during their stay. As it turns out, it’s not all that hard to dress Portland to the nines.
  • 400 SW Kingston Ave, Portland, OR 97205, USA
    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.