“Octagonal Oregon” – that should be the Beaver State’s new tourism motto.
This wondrous, diverse, nature-filled state in the Pacific Northwest has so many attractions and elite hotels that visits to eight distinct locations per trip should be a minimum requirement for any vacationer.
Whether your trip is centered on unforgettable hotels, family-friendly activities, museums, ocean beaches, waterfalls, mountains, the high desert, wine and beer tastings, whale watching, or hiking, Oregon won’t disappoint.
Day 1 – Central Coast
After landing in Eugene in the west-central part of the state, my family and I headed 60 miles due west to the coastal Florence area. The payoff: A dreamscape of white-capped waves, beaches, lighthouses, and sand dunes.
Near Cape Perpetua, easy walks reveal the mighty Thor’s Well, a gaping sinkhole that swallows the surrounding seawater, and the ocean geyser Spouting Horn, which spits water 30 feet high. Devil’s Churn produces thunderous water explosions due to its narrow shoreline channel.
Heceta Beach is set among steep mountainsides and near the photogenic Heceta Head Lighthouse. Encounter dozens of sea lions at Sea Lions Caves, a wildlife preserve and bird sanctuary. The Oregon Dunes National Recreation Area features a large expanse of temperate coastal sand dunes, with guided and king-size dune buggy tours offered by Sand Dunes Frontier.
Three Rivers Casino and Hotel offers adult fun with sit-down restaurants and a food court.
Day 2 – Northern Coast
The 160-mile drive up the Oregon Coast Highway (U.S. 101) from Florence to famed Cannon Beach offers an array of encounters.
The surf swirls inside a hollow rock formation shaped like a huge punch bowl in Devils Punchbowl State Natural Area, also popular for whale watching. Cape Kiwanda State Natural Area reveals a 340-foot monolith among orange-yellow sandstones and cliffs.
After a brief stop at the popular Tillamook Creamery for ice cream, free samples, and a factory tour, we explored Hug Point State Recreation Site, a sandy cove beach with tide pools, a small waterfall, and adjacent sea caves.
Five miles north, iconic Haystack Rock on Cannon Beach (photo above) awaits. Haystack Rock juts 235 feet high and dominates the breathtaking 4-mile-long sandy beach. The intertidal sea stack is in constant view while exploring the famous beach, named one of the most romantic getaways in the country.
The sophisticated Stephanie Inn, located on the beach, provides unparalleled panoramic views, top-rate dining, complimentary social hours, free chef’s breakfast buffet, and memories to last a lifetime. With fireplaces and views of the monolithic sea stacks rising out of the Pacific, the Stephanie Inn is the home of laid-back luxury. In addition to oceanfront and mountain-view rooms, there is the adjacent oceanfront Carriage House, which features gorgeous views from an open-concept living room and bedroom, private patio, king bed, and queen sofa sleeper. The suite features a gas fireplace, wet bar, generous soaking tub, and walk-in shower. My traveling party will never forget the amazing Carriage House and its walk-out views of Haystack Rock.
Day 3 – Far Northeast: Portland and Waterfalls
The cultural attractions in Portland, 80 miles east of Cannon Beach, are numerous, including Washington Park, which houses the colorful International Rose Test Garden, Portland Japanese Garden, and Oregon Zoo.
But make sure to visit the nearby Columbia River Gorge for an unforgettable afternoon of chasing waterfalls. Actually, most of the stops along the Historic Columbia River Highway include low-effort walks to the waterfalls, so “chasing” is minimal.
After admiring the river from above at the Vista House at Crown Point, stop along the highway for short-trek views of Bridal Veil Falls, Wahkeena Falls, Horsetail Falls, and the awe-inspiring Multnomah Falls (photo above). This two-step waterfall is one of the most beautiful in the nation, and at 620 feet, it’s the tallest in Oregon. The picturesque Benson Bridge traverses the creek between the two cascades, contributing to reasons why more than 2 million people visit Multnomah Falls annually.
Latourell Falls involves “chasing” – a 75-minute loop hike to visit its upper and lower falls. Reward yourself for burning calories at the nearby Gorges Beer Company, which showcases the scenery via a third-floor view (a “drink in the view” sign in the craft brewery perfectly captures the sentiment).
The new Hotel Vance in Portland is becoming a popular overnight option. It features funky décor and the good-vibes Beastro, a Korean restaurant owned by retired NFL star Marshawn “Beast Mode” Lynch.
Day 4 – Central: Smith Rock
Two hours southeast of Portland, past the thickly forested Cascade Range and stunning Mount Hood National Forest, the landscape suddenly changes to high desert. One hour later, we arrived at Smith Rock State Park (below photo) in central Oregon.
If we had closed our eyes, we would have sworn that we were in southern Utah. Pinnacles of volcanic ash rise up from the flat surface to create towering red and gold rock crags among deep river canyons. With several thousand climbing routes, including more than 1,000 bolted ones, Smith Rock is considered the birthplace of modern American sport climbing.
Hiking trails are just as popular, varying from easy to the moderate/difficult Misery Ridge Trail. My son and I conquered the trail, which provides a full tour of one of the state’s premier natural areas. Climbing 700 feet up from the Crooked River to the summit, we were rewarded with a close view of the Monkey Face spire, the centerpiece of the park.
Day 5 – Central: Brasada Ranch
Located 30 minutes south of Smith Rock and 30 minutes northeast of Bend, Brasada Ranch is the perfect spot to not only lodge, but spend time and soak in the high-desert playground.
Brasada Ranch is undoubtedly a deluxe resort, but the “ranch” portion of the moniker is accurate; untamed ranch land on 1,800 acres provides wide-open spaces and easy-on-the-eyes panoramic views of the nearby Cascade peaks, including the beloved snow-capped Three Sisters.
Of all our Oregon stops, this is where we felt most connected to the natural surroundings. Perhaps the remoteness contributed to those feelings. There’s nothing like an easy hike up to Spirit Rock, located on the premises, to soak in a sunrise, sunset, or the starry night sky with nary a sound of civilization.
This sanctuary offers award-winning golf, guided horseback riding, spa treatments, sports facilities, restaurants, and the friendliest resort staff one could ever meet.
In August 2023, Brasada Ranch supplemented its suites and cabins with the new Cascade Bungalows, featuring modern Scandinavian design, high ceilings, large fireplaces, private hot tubs, and panoramic windows offering sweeping Cascadian views.
Day 6 – South: Crater Lake National Park
Bluer than blue – that’s Crater Lake (photo below).
A two-hour drive from Brasada Ranch, Crater Lake is the deepest lake in the U.S. at 1,943 feet. It was formed 7,700 years ago from a volcanic eruption of a mountain; after the collapse of the summit, the caldera filled with water to form Crater Lake.
Rim Drive offers several pullouts and short walks to blue-hued views. Our favorite was the Sun Notch Trail (photo above), which features a 0.8-mile walk through a pleasant meadow surrounded by giant trees. The payoff: excellent vistas of Crater Lake, Wizard Island (a volcanic cinder cone in the lake), and Phantom Ship (a natural rock formation pillar that derives its name from its resemblance to a ghost ship).
Other park highlights include views from the Crater Lake Lodge and a short drive/hike to the Pinnacles, a group of volcanic pumice spires.
Day 7 – Northeast: Silver Falls State Park (with Bend bonus)
On the way back upstate, we visited Bend, which deserves its reputation for culinary and brewed delights, clean-city atmosphere along the mighty Deschutes River, and ultra-coolness.
A hike or drive up to Pilot Butte State Park, a 500-foot cinder cone in the middle of town, offers 360-degree views of snow-covered peaks and high-desert plateaus. The High Desert Museum explores the history and culture of the wild West. Bend even has the last Blockbuster Video store in the world.
But our main destination was Silver Falls State Park, 2½ hours northwest of Bend. Silver Falls is a gem that outsiders know little about but Oregonians cherish. The park features an astounding 10 gushing waterfalls that visitors can hike to and under.
Its most famous feature, the 177-foot South Falls (photo above), is only steps away from the parking lot. After admiring the breathtaking view from above, visitors can descend into a cave behind the falls for an amazing experience along the Maple Ridge Loop. Those seeking more adventure can traverse the 5-mile Winter Falls Loop to see close-up views of seven waterfalls or the 7.2-mile Trail of Ten Falls to see all of them.
Day 8 – West Central: Williamette Valley and Eugene
Silver Falls, nearby Salem, and the area all the way to Eugene (75 minutes southwest) is vast, fertile vineyard country, so tastings at the 400-plus wineries are the draws.
Eugene is home to the University of Oregon and 175,000 residents. The campus showcases sleek buildings and sports facilities for track and field, football, and basketball.
Skinner Butte Lookout rises 240 feet above nearby neighborhoods, reaching 682 feet above sea level and providing a full view of downtown and beyond, including sunsets.
A top meal option is Our Daily Bread Restaurant in nearby Veneta. Located in a former church, it features high, stained-glass windows. The homey establishment features top-notch sandwiches and an adjoining bakery with mouthwatering cinnamon rolls.
Future ‘Octagonal Oregon’ Vacations
My trip tapped into just a small portion of what makes Oregon grand. There is so much more to discover: Painted Hills and the rest of eastern Oregon; the far northern and entire southern portions of the 363-mile coast; Klamath Falls; the 54,000-acre Newberry National Volcanic Monument with lava flows, lakes, and waterfalls; 11 national forests; 21 national wildlife refuges; 361 state parks; and 3,764 mountains, including Mount Hood, which deserves more than just a drive-by.
I will be going back for more. It turns out that eight is not enough.
