Oregon Travelers Recommend

A full Portland experience can be had in three days with an itinerary that combines the sights, culture, and adventures of Oregon’s largest city. Here are our top ideas for how to spend your time in Portland and its Pacific Northwest surroundings, including day trips to the mountains or wine country.

Day 1: See the City Sights

Explore Portland at your own pace on a hop-on hop-off trolley tour that allows you to visit the attractions that most interest you, such as Powell’s Books or Pioneer Courthouse Square. Allow time to discover Portland’s food scene: perhaps by taking a coffee and doughnuts tour, food cart tour, or a food tour of Mississippi Avenue. Beer and wine lovers can visit breweries or urban wineries on a bike tour, or skip food in favor of filming locations from the TV show Portlandia. More brews can be enjoyed in the evening on a haunted pub tour of the once-seedy Old Town district.

Day 2: Explore Portland Outdoors

Visit one of the largest urban forests in the country on a guided hike of Forest Park in northwest Portland, and then take to two wheels to explore Portland like a local with a bike tour along the Willamette River waterfront, through the green spaces of the Park Blocks, and into the popular Pearl District. For a more adventurous pursuit, head to the White Salmon River in Washington, a little over an hour north of Portland, for whitewater rafting. When evening rolls around, hop on a dinner cruise to admire the city from the waters of the Willamette, or perhaps ride through downtown on an evening Segway tour.

Day 3: Go Beyond the City Limits

Tucked among mountains, rivers, vineyards, and the Pacific Ocean, Portland is brimming with day trip options. Head west to visit the coastal towns of Cannon Beach and Manzanita, go south to enjoy pinot noir and other varietals in the Willamette Valley wine region, or travel north into Washington to see Mount St. Helens, an active volcano. The most popular day trip, however, is east of Portland along the Historic Columbia River Highway. Tours typically take you to several natural attractions including Multnomah Falls, the tallest waterfall in Oregon; the Columbia River Gorge, a popular windsurfing and kitesurfing destination; and Mt. Hood, the highest mountain in Oregon.

With a compact central area and quick access to the surrounding Pacific Northwest landscape, Portland is an ideal city to explore in just one day. From historical architecture to a hip culinary scene to nearby waterfalls, there are a variety of ways to make the most of your limited time in Oregon’s largest city.

Morning: See the Sights

Head out on a hop-on hop-off tour by trolley to see Portland’s top sights at your own pace. Visit attractions that most interest you, such as Pioneer Courthouse Square or Powell’s Books. If you prefer a guided experience, opt for a morning city tour, which shows you the best of Portland in a half-day, or get your caffeine fix on a coffee and doughnut tour. Alternatively, you can discover the natural wonders just outside Portland on a morning tour to Latourell Falls, Bridal Veil Falls, and Multnomah Falls, the tallest waterfall in Oregon.

Afternoon: Discover the Tastes

Now is the time to indulge in the array of food and beverage options in Portland, where there’s something for every palette. Beer lovers can check out local breweries on a bike tour while wine enthusiasts can explore urban wineries and tasting rooms on a bike tour of their own. Different neighborhoods can be explored on food tours of downtown or Mississippi Avenue, or experience the city’s food truck and carts culture. If you’re a fan of Portlandia, don’t miss the chance to see places from the show on a film locations tour.

Night: Explore More

Put an eerie spin on a night out with a haunted pub tour that includes beer samples in the Old Town district, a neighborhood once home to nefarious activities, or perhaps hone your photography skills on a nighttime tour of Portland with a photographer guide. If you prefer to experience Portland from the water, hop on a dinner cruise along the Willamette River.

Two days in Portland gives you enough time to see multiple sides of the city, from its food culture to its interesting neighborhoods, lush natural beauty, and active lifestyle. Here are a few ways to create an itinerary that suits your interests.

Day 1: Sightseeing and Local Experiences

Morning: Book a hop-on hop-off trolley tour to see Portland at your own pace, which allows you to visit the attractions that most interest you such as Powell’s Books or Pioneer Courthouse Square. If you prefer to explore with a guide, opt for a morning city tour or a coffee and doughnuts tour.

Afternoon: Enjoy Portland’s culinary delights on a food carts tour, a breweries or urban wineries bike tour, or a food tour of a specific neighborhood such as downtown or Mississippi Avenue. Alternatively, see places from the cult hit Portlandia on a tour of the show’s film locations.

Night: Head to the once-seedy Old Town district on a haunted pub tour that includes beer samples, or learn how to take photos at the trickiest time of day on a nighttime photography tour, where a photographer guide gives you tips on capturing shots at dusk and dark.

Day 2: Get Out and Active

Morning: Discover the natural wonders just outside Portland on a morning tour to Latourell Falls, Bridal Veil Falls, and Multnomah Falls, the tallest waterfall in Oregon. Or stay in the city to take a guided hike of Forest Park, one of the largest urban forests in the country.

Afternoon: Do as the locals do with a bike tour of Portland that takes you along the Willamette River waterfront, through the green spaces of the Park Blocks, and into the popular Pearl District. Or, for something more adventurous, head to the White Salmon River in Washington for whitewater rafting.

Night: Admire the city lights of Portland from the water on a dinner cruise along the Willamette River that includes Pacific Northwest-inspired cuisine and live entertainment with a full bar on board. Or book an evening Segway tour of downtown to zip through this district without the daytime crowds.

With more than 200 wineries and a location less than an hour’s drive from downtown Portland, the Willamette Valley is a prime wine tasting destination in Oregon. Here’s everything you need to know about sampling the region’s best wines on a tour.

Highlights

• Visit a handful of wineries and get the chance to meet with winemakers or have a sommelier as your guide, depending on the tour you choose.

• Some wine tours from Portland offer hotel pickup and drop-off, and all provide transportation from the city to the wineries so you can relax and enjoy the ride.

• Tours may include snacks or a full lunch along with wine tastings, while some provide lunch but you’ll need to pay for your own tasting fees. Inclusions vary, though in most cases, wine tastings are included.

• Some tours combine wine tasting with other experiences, such as a visit to see waterfalls or taking a taking an early morning hot-air balloon ride over Oregon wine country.

Things to Know

• Dundee and Newberg, two popular Willamette Valley towns, are each located about 28 miles (45 kilometers) from Portland.

• The most famous varietal in the Willamette Valley is pinot noir, but it’s by no means the only great wine in the region. Others to try include chardonnay, pinot gris, riesling, cabernet franc, and viognier.

• Tours typically last between five and nine hours, depending on the distance traveled and number of wineries visited in a day.

• Not every tour includes water or snacks, so it’s a good idea to be prepared with your own.

Situated in central Oregon at the base of the Cascade foothills, Bend’s geography makes it an outdoor playground. From mountain biking, cycling, and hiking to kayaking, rock climbing, and skiing, Bend offers nearly every type of outdoor adventure. Here are some ideas on how to make the most of one day in Bend. 

Morning: Hike to a Waterfall or Ancient Volcano

Jump start your visit to Bend on a hiking or mountain biking tour of the mountains just outside of town. The hike to Tumalo Falls is a locals’ favorite—plus, the viewpoint to see the main waterfall is just a few steps from the parking area, making it ideal for hikers of all abilities. 

If you feel like venturing further afield, check out the ancient lava flows and cinder cones of Newberry Volcanic National Monument. Consider taking a photo tour to learn how to perfectly capture the wild desert landscapes that surround Bend. 

Afternoon: Explore the Deschutes River

In the early 1800s, pioneers heading further west would cross the Deschutes River at Farewell Bend, where a makeshift community eventually became the city of Bend. The Deschutes River is still the heart of Bend, and watersports options are plentiful. Kayak, float, tube, or stand-up paddle board down the river, or visit the Bend Whitewater Park where kayakers will find a white-water playground right in the river. Alternatively, explore the Deschutes River Trail, which begins near the Old Mill district and meanders along the shores of the river or take a guided fly-fishing tour. 

Evening: Sample Brews on the Bend Ale Trail

With over 20 microbreweries within the town limits, Bend’s prolific craft beer scene is what draws many visitors to the city. Before heading to the breweries, it’s worth checking out the top of Pilot Butte—which you can drive to during the summer months and hike anytime of year—to catch the sunset over the Cascades. If you can’t wait to sample the beer, you can also catch sunset from the Crux Brewery patio. Pick up a Bend Ale Trail passport from the Bend Visitor Center and receive a commemorative pint if you collect enough stamps.