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72 Hours in Portland

Written by Sandy Bornstein

This blog post was updated on July 20, 2021.

First-time visitors will appreciate Portland’s mild climate, but may want to avoid its cloudy and rainy winters. They will feel at home in the downtown area that is well known for its coffee shops, microbreweries, food options, and cultural events.

After a day of discovering metro Portland, adventure seekers can explore the adjacent terrain by driving to three of the Seven Wonders of Oregon—the Historic Columbia River Highway Scenic Byway, the Mt. Hood Scenic Loop, and the northern section of Oregon’s Coast.


Washington Park Attractions

Portland is a city that can be discovered by foot. Don’t forget to include the Washington Park area on your route. Be aware that it’s a steep uphill walk from most hotels.

Families can start at the southwest corner with the Oregon Zoo, the Portland Children’s Museum, and the World Forestry Center. Nature lovers, on the other hand, can go to the eastern section for the spectacular Portland Japanese Garden and the aromatic Rose Garden. Keep in mind that the time of year may affect your viewing.

A few historical elements are scattered throughout the grounds. Look for the Holocaust Memorial, the Sacajawea Statue, the Vietnam Veterans Memorial, and the lesser-known Coming of the White Man. Well-marked hiking paths connect all of the key areas and the Wildwood Trail leads to Pittock Mansion.

Portland Japanese Garden 1 S Bornstein

Image via Sandy Bornstein

Pittock Mansion

Step inside the Pittock Mansion and explore the 23 antique rooms. You’ll leave with an understanding of Portland’s past. On a clear day, you’ll have an incredible view of Portland’s skyline that includes a backdrop of mountains, bridges, forests, and rivers.

Powell’s City of Books

Book lovers will rejoice at this Pearl District location that ranks as the world’s largest used and new bookstore.

Food Carts, Coffee, Restaurants, & Breweries

For meals on the go, try one or more of the strategically placed food carts. Wolf and Bear’s is a Mediterranean option. Fish lovers will be lured to Fishbox’s wild caught local salmon. Keep an eye out for street vendors. There’s no shortage of ethnic food choices in Portland.

Coffee is another staple of Portland life. Stumptown Coffee Roasters, Barista, and Case Study Coffee are reliable choices. Tea and pastry mavens may choose Maurice as an alternative

Portland addresses the needs of most diners. Make a reservation at Departure for a special dinner with a 15th floor view of the city. Travelers seeking Italian fare should reserve a table at Ava Gene’s or order a pizza baked in the wood-fired oven at Ken’s Artisan Pizza.

Don’t forget that Portland is also known for its microbreweries. Deschutes is one place to consider.


Landmarks and Waterfalls

Multnomah Waterfall S Bornstein (1)

Image via Sandy Bornstein

By visiting the official website, you can plan your journey to the Historic Columbia River Highway Scenic Byway. This useful site includes maps and information regarding waterfalls, hiking trails, picnic areas, visitor centers, and estimated travel times. While its unlikely that you’ll have time to visit every designated spot, look for Chanticleer Point at the Portland Women’s Forum Overlook, the Vista House, Latourell Falls, Bridal Veil Falls, Wahkeena Falls, and of course Multnomah Falls.

Mt. Hood Scenic Loop and Fruit Loop

Adventurers who would also like to see Mt. Hood can exit at Hood River, a windsurfing and kite-boarding mecca. This town has dozens of casual dining restaurants, several coffee shops, and Mike’s Ice Cream.

Continue your journey by taking Highway 35 to Mt. Hood, the highest peak in Oregon. Along the way, you will pass dozens of orchards and wineries in the Fruit Loop. After arriving at Mt. Hood, stroll through the Timberline Lodge. This remarkable landmark dates back to the Great Depression. It runs the longest lift operated ski season in North America.

Jonsrud Viewpoint

On the way back to Portland, take a small detour in the town of Sandy. Look for the signs for Jonsrud Viewpoint. This special spot provides a tidbit of history along with a panoramic view of the region.

*Note: A rental car or prearranged tour is required to enjoy these activities


Ecola State Park

Take Highway 26 East to Highway 101, a coastal highway. Be patient. Logging trucks and other slow moving vehicles may slightly delay your arrival. Look carefully for the signage for Ecola State Park between Seaside and Cannon Beach. This well maintained site offers hiking trails and a cliff where you can take spectacular photos of crashing waves and wildlife.

Canon Beach

Drive a bit further to Cannon Beach. Weather permitting, you can prance on the 4-mile beach and see the Tufted Puffins and colonies of sea birds that nest on Haystack Rock. A large number of gray whales can be seen during the spring and winter. In the fall, Roosevelt Elk graze in meadows. The Cannon Beach Magazine (compliments of the Cannon Beach Chamber of Commerce) and the website provide suggestions for restaurants and activities.

Beach Access from Oswald West-South Trailhead S Bornstein (1)

Image via Sandy Bornstein

Oswald West-South Trailhead

As you continue on Highway 101, there will be numerous photo opportunities, campsites and trailheads for hiking. By early afternoon, the fog may roll in and limit visibility near the coast. At the Oswald West-South Trailhead, you can walk over a hanging bridge and follow a path that leads to a secluded beach area.

Tillamook Cheese Factory Tour & Ice Cream

Before reaching Highway 6 that leads back to Portland, take a self-guided informative tour at the Tillamook Cheese Factory. Indulge by ordering a creamy ice cream treat. Enjoy the countryside as you drive back to Portland.

Tillamook Cheese Factory Tour S Bornstein

Image via Sandy Bornstein

*Note: A rental car or prearranged tour is required to enjoy these activities

Are you a local or know the area well? Tell us about any other must-do things that we may have missed!

About the author

Sandy Bornstein

Sandy Bornstein lived as an expat in India. Her award-winning memoir, May This Be the Best Year of Your Life, highlights what she learned as the only American teacher at an international Bangalore school. After living abroad, Sandy continues to explore the world and write about her travels. You can follow Sandy's adventures at

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1 Comment

  • The waterfall looks mesmerising. Great information. Thanks for sharing.