This Action-Packed City Is the Northwest's Favorite Getaway Spot

Portland’s NBA team kind of gives it away. The Trailblazers make it clear that this is a city defined by its outdoor opportunities. There are more than 200 trails in the Portland area. From the city, you can see three volcanic peaks in the mighty Cascades—nearby Mt. Hood, and in neighboring Washington state, Mt. Adams and Mt. St. Helens (or what’s left of that last summit after it blew its top in 1980). Drive an hour to the Columbia River Gorge National Scenic Area, and your outdoor rambles reach spectacular heights, with vistas in all directions and waterfalls plunging from sheer cliffs. There are a boggling 90 major falls and countless minor ones in the park, thanks to the rainy traditions that make for green forests and gardens in these parts.

Related: California's Most Underappeciated Adventure Hotspot Is Also Its Easiest to Reach

Back in Portland, it’s raining beer. Oregon's largest city has more than 60 craft breweries and, for good imbibing measure, more than a dozen urban wineries—giving you ample beer- and wine-tasting possibilities. The concentration of outdoor activities (including biking, windsurfing, and kiteboarding) and indoor recreation is part of the city’s emphasis on living life—on the worth ethic, not just the work ethic. There's no shortage of things to do in Portland that will happily affirm this for visitors during three unforgettable days. 

Portland makes for a great place to immerse in the art of life-tasting. That includes a host of cultural offerings, from blues, jazz, film, and beer festivals to a solid lineup of distinctive museums. The Portland Art Museum is one of the oldest in the country, featuring major exhibits from around the world and one of the nation's deepest collections of Native art. For a primer on the local mountains and geology, check out the Rice Northwest Museum of Rocks and Minerals.

Most of all, Portland is the perfect city for exploring, adventuring, learning, and indulging at your own relaxed pace. Here's how to go with the flow in a one-of-a-kind town built on that very concept—right down to the two major rivers which intersect here, the Columbia and Willamette.

How to Get to and Around Portland 

If you’re coming from a distance, flying is going to be the best route. Visitors land at Portland International (PDX). There are several options to get from the airport to the city—bus, Uber, taxi, and MAX. The MAX train is a great choice, taking you direct from the airport to downtown, where you can catch a bus, cable car, or ride share vehicle. Portland has excellent public transit, which makes it easy to get around. If you're driving, the main route from the north or south is Interstate 5, but there’s a bypass route, I-205, that leads into the city with less traffic from the east, north, and south.

When to Visit Portland

You’ll want to bring some cold-weather gear in late fall and winter, but Portland has its many charms during the cooler months, with winter sports and excellent skiing at nearby Mount Hood. High temps in mid-winter are brisk, ranging from mid 30s to high 40s Fahrenheit. The City of Roses, as Portland has been known for 100 years, gets its famous share of precipitation to generate those blooming buds. If you want to see thundering waterfalls, aim for a spring visit, when the city's multitude of cascades are frothing. Summer is always a popular time for a Portland visit, with June-through-August temps generally hanging in the mid-80s.

Where to Stay in Portland: Best Hotels

Located in Portland's downtown business section, the down-to-earth Hotel Zags has its mind on the business of adventure and making sure guests have what they need for a participatory visit. The Gear Shed at the hotel has bikes and skateboard rentals, outdoor equipment, fishing gear, and more. They know why you’re here. On top of all that, the room rates are some of the best in the city. 

A boutique hotel with Old World feel, Hotel Lucia also delivers great service at a reasonable rate. Sporting a large photography collection and art, the Lucia has been a gathering place since 1909 and is on the National Registry of Historic Places. If you’re looking for a room with a view, the River’s Edge Hotel, a Hilton property, gives you a relaxing perch overlooking the Willamette River.

Where to Eat in Portland: Best Restaurants

You can find plenty of great eateries in Portland, many of them farm to table fresh. To get more than a flavor of Portland seafood tradition, check out Jake’s Famous Crawfish, which has been holding down the fort on dishes from the sea here for 127 years. From the vintage photos on the wall of the bar to the unpretentious tables, you're part of history and a very tasty present at this 12th Street institution, from the steelhead trout to the fish stew. Come early for happy hour. 

Over in the Killingsworth district, Gabbiano’s has quickly established a rep for great Italian comfort food. No reservation required. This is an old-style walk-in spot serving the sort of hearty North Beach, San Francisco-style Italian restaurant fare that co-founder David Sigal grew up with. The latest creation of Portland serial Thai restaurant starter Akkapong Earl Ninsom, Hat Yai specializes in southern Thai cuisine, and is winning fans with dishes from shallot fried chicken to its tasty roti, curry, and spicy ground pork.

Where to Drink in Portland: Best Bar

Since you're on vacation, why not hang at a bar whose drinks can make you feel far-flung? The Hey Love, inside the Jupiter Next Hotel in the Buckman district, accomplishes this with an assortment of drinks that evoke tropicalia and foreign lands (try the festive strawberry tequila Negroni)—not to mention various pop music eras, from the Papa Don’t Peach mojito to a Oaxacan Sunrise served in a cactus. 

Don’t Miss: Top Attraction in Portland 

The Colorado River sculpted its way through the wilds of Arizona millions of years ago, leaving canyons in its wake. Up here in Oregon, monumental ancient floods and volcanic activity helped shape the Columbia River Gorge. The resulting landscape is not to be missed for sheer scale, massive vistas, and the stunning waterfalls crashing off its cliffs. You’ll want to spend time here taking in the spectacular sights, such as Multnomah Falls, which pours down 620 feet. You’ll think you are in Kauai, cascade-wise.

Savvy Tip for Visitors to Portland

Portland has been rated the most bike-friendly city in the nation, with more than 350 miles of bike paths. While far less than one percent of people in America's 100 largest cities commute to work by bikes, over five percent of Portlanders pedal to their jobs. This makes Portland one of the best places to explore on a bicycle. Rent one for a day and get to know the city from pavement to trail and forests within the city limits.

Things to Do in Portland Over Three Days

Day 1: Cruise the Gorge, Gape at Waterfalls, and Shoot the Breeze at Hood River

There’s no doubt about the first stop on the itinerary. Jump in the car for the 26-minute drive east on Highway 84 to the Columbia River Gorge overlook at the century-old Crown Point Vista House. The viewing station is a combined museum and observatory perched above the river, with 360-degree views of the massive river and cliffs. Awe is the order of the day as you contemplate the looming bluffs of the Columbia Plateau, formed six to 16 million years ago by the largest volcanic lava flows in the history of the Northwest, and which changed the course of the mighty Columbia. 

The river is almost an inland sea or fjord, and it’s not because it rains a lot here. There are 10 main tributaries emptying into the river, including the Snake, Willamette, and Deschutes. Head east on the highway, and you have an assortment of monumental waterfalls to choose from, including the highest, Multnomah Falls. Do your neck-stretching exercises and make your way to Latourell Falls, which stands in at 224 feet, and Bridal Veil Falls off I-84. Both involve short hikes to access. You can catch Wahkeena Falls from a viewing platform right off I-84 or hike up a trail to see its three cascades up close. 

The next stop along the river is one of the premiere windsurfing and kiteboarding hubs, Hood River. If it’s windy, grab a board and give it a go or just hang out at the local tavern, Full Sail Brewing, and watch the experts dance on the river. You can top off the day’s adventures back in Portland with some pasta at Gabbiano’s and music at the Kenton Club, featuring rock and indie.

Day 2: Hike in the Trees, Admire Art, and Take a Brewery Tour

Start your day in Portland with one of the many great hikes in the city, the Council Crest Trail. The trail starts at the Marquam Nature Park trailhead and takes you up through a cornucopia of Oregon forest denizens, from western hemlock to big leaf maple to fir trees. The trail is about an hour in length and, as you wind up to the top of the crest, you’ll have great views of the city and on a clear day the snow-capped cones of Mt. Hood and Mt. Rainier. 

Now that you've worked up an appetite, make your way to the Tin Shed Garden Café on Alberta St., where you can dig into eggs and raspberry scones. Next stop is the Portland Art Museum, a superb destination in its own right, but we’re heading first to the second and third floors for the Center for Native American Art, where you will see one of the best collections of Native art in the U.S. One collection, the Confederated Tribes of Grand Ronde Center for American Art, has over 3,400 pieces from tribes around the U.S. There’s also a relatively new wing, the Center for Contemporary Native Art, which showcases modern Native artistry. 

You can’t be in the brewpub capital of the U.S. without exploring its offerings. Take your choice of brewery tours from Wayfinder Beer on 2nd Avenue, specializing in cool fermentation and making beer that coaxes malt complexities to the surface. Or Breakside Brewery, owner of multiple gold medals and voted the “best beer in Oregon' by The Oregonian. There's also the super-popular Great Notion, home to bold and hoppy flavors. You can wrap things up with a dinner and a local band at one of the leading musician hangouts, Mississippi Studios and Bar.

Day 3: Do the Fruit Loop, Go Wine Tasting, and Board a Riverboat

The beautiful surroundings extend beyond the Columbia Gorge and hiking trails in the city. A short drive from the city, you can explore scenic orchard lands on the Hood River County Fruit Loop, which is 35 miles in length. You’ll want to stop and sample the farm fresh fruit, jams, jellies, and pastries. That’s going to make you thirsty, but you have your pick of wineries to wash it down. 

With a stunning 877 wineries in the Portland region, you will have plenty of refreshments to choose from. Villa Catalana Cellars, 30 miles to the south of Portland, has an assortment of syrah, pinot noir, and merlot to sample. You can bring your lunch with you or opt for one of the winery’s wood-fired pizzas. The grounds are impressive, the stone-and-tile main structure modeled after a Spanish church. 

Closer to the city, just 15 minutes outside Portland in the foothills of the Tualatin Mountains, you’ll find Helvetia Winery, which offers a tour, tasting, and a history of winemaking. Wines range from pinot noir to merlot and pinot gris. The city of Portland is also stocked with wineries. Check out the Portland Wine Company, which features a vintage Wurlitzer jukebox and eclectic music, as well as Garageland rose or Antsy Pants Reserve pinot noir. 

By mid-afternoon it will no doubt be time to take a seat. You can take a load off on a river cruise on the Columbia. See the Bonneville Dam, Native American fishing platforms, and more gorgeous gorge scenery, and let someone else do the driving. After a one-hour cruise, cap off your weekend with a scrumptious dinner of southern Thai offerings at Hat Yai. You have now completed your living large mission in Portland. The last pre-departure task will be planning your next visit.