Seven Wonders of Oregon

You can tell how well Portland is loved by the plethora of nicknames bestowed upon her: Rose City, City of Bridges, Portlandia and Beervana. Take at least two days to explore this friendly, energetic city that’s cradled between the Willamette and Columbia rivers.

Start in the Pearl District on the city’s west side, where you’ll find one-of-a-kind boutique shopping at stores like Made Here, Canoe, Radish Underground and Frances May. Don’t miss Powell’s City of Books, a labyrinthine book wonderland and the largest independent used and new bookstore in the world.

For lunch, hit the downtown food cart pods — there are more than 500 to choose from in town, serving cuisine from around the globe. Park yourself at Pioneer Courthouse Square — aka Portland’s living room — for excellent people-watching, then take a stroll across the Hawthorne Bridge to the Vera Katz Eastbank Esplanade on the east side of the Willamette River.

Spend the afternoons exploring the Alberta neighbourhood in North Portland — home to the Alberta Rose Theatre, Salt and Straw ice cream shop and a host of cafes, restaurants and shops.

Collect your car this morning and take the scenic route on Historic Highway 30 from the heart of Portland to your first Wonder, the Oregon Coast. This route will take you north past Sauvie Island, where you can stop at roadside farm stands and berry fields to enjoy some local flavour. Stop off in Scappoose Bay for some flat-water kayaking on the Columbia River. The highway hugs the river, passes the Lewis and Clark National Wildlife Refuge, and brings you into the charming town of Astoria. With dozens of Victorian-era homes perched on the steep hillside above the bay, it’s easy to see why some call this town “Little San Francisco.”

Start by visiting the Astoria Column for panoramic views of the Columbia River and surrounding landscape. Afterward, explore the Columbia River Maritime Museum to learn about the region's rich maritime history. Take a stroll along the Riverwalk, enjoying scenic views and passing ships. For dinner, head to one of Astoria's waterfront seafood restaurants, like Bowpicker Fish & Chips or Bridgewater Bistro, for fresh, local fare. End the evening with a sunset at Fort Stevens State Park or enjoy a local brew at a cosy Astoria pub.

From Astoria, head south on Highway 101, the Pacific Coast Scenic Byway. The drive alone is one for the bucket list. With the ocean on your right and the steep cliffs and forest on the left, the Coast highway delivers awe-inspiring views, each more beautiful than the last and replete with towering sea stacks, pristine sandy beaches and the endless crashing surf.

On the way to Newport, stop in Fort Stevens State Park, 4,200 acres of forest and trail with great options for hiking and biking. Take time to check out the Peter Iredale shipwreck, a four-mast steel sailing vessel that ran aground here in 1906.

Stop in the charming town of Wheeler on the Nehalem Bay for a bite to eat or to browse the antique shops. Veer off Highway 101 at Tillamook to tour the Three Capes Scenic Loop. This detour will take you past the Cape Meares Lighthouse and Cape Lookout State Park and down to Cape Kiwanda in Pacific City, where you can settle in on the Pelican Pub & Brewery patio to drink a beer and watch surfers ride the waves.

Onward to Lincoln City, you’ll find some of the best wind for flying kites on the Coast. The annual kite festival takes place in June and highlights expert kite demos, kite making for kids and some of the biggest, most unique kites in the world. At Devils Punchbowl State Natural Area, you can peer down inside a large bowl carved out of the stone by the dramatic churning of the ocean.

Head on to Newport, where you’ll find the beautiful, accessible tidepools of Yaquina Head Outstanding Natural Area.

Spend some time exploring Newport’s historic bay front and Nye Beach neighbourhoods. At the bay front, wander among the boat docks of this working seaport town and sample fresh catch at local restaurants. Nye Beach is home to quaint shops, the famous, book-centric Sylvia Beach Hotel and beautiful stretches of sandy beach perfect for beachcombing or fat biking.

A scenic detour inland along the Yaquina River will take you to the little town of Toledo, home to Pig Feathers BBQ, Twisted Snout Brewery and an annual wooden-boat show.

Back down scenic Highway 101, head south past Yachats to Cape Perpetua, where the Siuslaw National Forest juts out over the ocean in a forested headland. You can hike or drive to the breathtaking viewpoint at the top.

Farther south, the Oregon Dunes National Recreation Area stretches for 40 miles between the towns of Florence and North Bend — the largest expanse of coastal sand dunes in North America.

Just outside of Charleston, Sunset Bay State Park affords dramatic and beautiful views that make the rugged South Coast famous. This park is adjacent to Shore Acres State Park and Cape Arago State Park, each offering opportunities for hiking, whale watching (seasonally) and storm watching.

Onward into the town of Bandon, be sure to stop at Face Rock Creamery, where you can watch the cheesemakers at work, sample a variety of award-winning cheddars and top off the day with a big scoop of Umpqua ice cream.

This day will be your longest yet in the car, but you’ll check two Wonders off your list as you hit the final bit of the Coast and visit Crater Lake. Linger in Bandon for breakfast and a bit of shopping in Historic Old Town, including Coastal Mist chocolate shop, offering an array of delectable handcrafted confections and desserts, as well as drinking chocolates and drinking caramels.

At Port Orford Heads State Park, hiking trails along the bluff take you to views of migrating whales, seabirds and local fishing boats. Visit the free museum housed in the 1930s Port Orford Lifeboat Station here.

Continue on to the town of Gold Beach, visit the mouth of the Rogue River as it enters the ocean, and take a stroll at South Beach and Buena Vista state parks.

South of the town of Brookings and inland is where you’ll find the Oregon Redwoods Trail, which winds through a grove of majestic, towering redwoods, the only coastal redwoods found in the Pacific Northwest.

Say goodbye to the Coast as you head farther inland toward the Oregon Caves National Monument & Preserve and take a tour of these unique marble caves formed over the ages by dripping rainwater. (Note: Tours are given on a first-come, first-served basis, and self-guided tours are not allowed.)

Head into the town of Medford for a taste of Oregon craft beer, a bite to eat or a live performance at the Craterian Theater at the Collier Center for the Performing Arts.

Then you’ll be on your way to Crater Lake, where the 33-mile drive around the rim offers various viewpoints of the gorgeous crystal-blue waters of the caldera lake and the cinder cone in the centre, called Wizard Island.

Take in the quiet beauty of this special place at sunset and sunrise. In the morning, hike the trail down to the water, or bike the rim road.

Then it’s time to head north to the town of Bend. This sunny outdoor recreation mecca is also home to the Old Ironworks District, an enclave of artists and makers housed in a 1912 railroad building. Do some shopping for one-of-a-kind finds here (and don’t miss tiny Sparrow Bakery).

Lace up your hiking boots or snap on your bike helmet and hit the Deschutes River Trail. Following the river and running through the heart of town, the 19-mile trail system offers several points of entry for hiking and biking.

Beer lovers won’t want to miss the Bend Ale Trail, your guide to 14 of the area’s craft breweries. And Bend’s walkable downtown core is a great spot to get drinks and dinner, take in a show or do a bit of shopping.

Get ready for two more Wonders! You won’t be driving far today, but it will take you some time to get where you’re going.

Head north out of Bend on Highway 97 to the town of Redmond. The restored downtown recently saw the arrival of Wild River Brewing and eagerly awaits the reopening of the Historic Redmond Hotel, a 1928 building slated to get a new lease on life from a Portland developer.

Then it’s on to Smith Rock, which will stop you in your tracks with its beauty. The tuft and basalt spires have drawn world-class rock climbers since the 1980s. You can watch climbers scale the red rock on hundreds of climbing routes, or go for a hike along miles of hiking trails to admire the pretty Crooked River and the high-desert landscape.

Get ready for your fourth Wonder when you head to the Painted Hills, located about 90 minutes east of Smith Rock on Highway 26 and part of the John Day Fossil Beds National Monument. Here you’ll find yet another otherworldly landscape, the undulating earth unfolding in hues of ochre, gold and green, formed by volcanic activity 35 million years ago.

Farther east, you’ll find the Thomas Condon Paleontology Center, a working research and interpretive center with the second most complete fossil record in the world, documenting the past 55 million years.

For a more recent history lesson, don’t miss the Kam Wah Chung State Heritage Site in John Day, a veritable time capsule of an early 20th-century Chinese apothecary shop on the site of what was once Oregon’s largest Chinatown.

Head northeast out of John Day on Highway 7 toward Baker City. In the fall, the gold larch trees shine brightly out of the forest on this quiet country road, which is part of the Journey Through Time Scenic Byway.

Stop in Prairie City for a cup of coffee, a bite to eat or an overnight at the charming Historic Hotel Prairie. Be sure to spend some time at the Sumpter Valley Dredge State Heritage Area at the base of the Elkhorn Mountain Range. This waterway was the lifeline of the mining industry here more than 100 years ago.

Head north into the mountains toward Anthony Lakes Mountain Resort. In summer the hiking and mountain biking here in the Elkhorns is undiscovered and unparalleled; in winter the family-friendly ski area has downhill skiing as well as miles of Nordic track and great backcountry access.

Onward to Baker City, where you can explore the history of the Oregon Trail at the National Historic Oregon Trail Interpretive Center, where you’ll learn the story of the 400,000 pioneers who came west between the 1830s and 1860s. Take a self-guided walking tour of Historic Baker City with a map from the chamber of commerce, which outlines the more than 100 buildings of historic significance in this classic western town. Don’t miss the beautifully restored Geiser Grand Hotel, Barley Brown’s brewpub and Peterson’s Gallery and Chocolatier.

Get ready for your fifth Wonder! Today’s itinerary will land you at the foot of the Wallowa Mountains, aka “Little Switzerland,” whose snowy peaks reach nearly 10,000 feet.

Head west on I-84 and then north on Highway 237 to the town of Union, home to the historic Union Hotel and Buffalo Peak Golf Course, and close to Catherine Creek State Park.

Along the way to Joseph, you’ll pass through Hot Lake (home to the Hot Lake Springs, a historic mineral springs resort and now bronze gallery), as well as Lostine and the town of Enterprise, where you’ll find the Maxville Heritage Interpretive Center. This museum tells the little-known story of an African American logging town that once existed north of here during the 1920s and 1930s.

Stop in the town of Joseph to enjoy a number of shops, restaurants and brewpubs, as well as a craft distillery and a chocolate shop. Pay a visit to the Old Chief Joseph Gravesite, a sacred site for the Nez Perce people at the confluence of the Wallowa and Lostine rivers.

Take this day to explore in and around the majestic Wallowa Mountains. Start in the town of Joseph, which has made a name for itself as a centre for bronze art. You can browse the galleries and public art on foot.

Make your way to nearby Wallowa Lake, where you can enjoy a picnic on the shore, paddle a boat or ride in the Wallowa Lake Tramway, which takes you up to the top of Mt. Howard at 8,000 feet for views of the entire Wallowa range.

Go for a hike in the Eagle Cap Wilderness, where trails offer rugged backpacking routes or moderate day hikes. No matter which of the dozens of trails you choose, you are certain to find yourself more alone than you would on the western side of the state.

For views of the dramatic gorge on Oregon’s border with Idaho, don’t miss the Hells Canyon Overlook. You can continue on this road to drive part of the Hells Canyon Scenic Byway. (The entire route is 213 miles in total, starting in La Grande, circling through Joseph, then south to Halfway and Baker City.) Take some notes and start planning a multi-day rafting, hiking or fishing trip into Hells Canyon.

Goodbye, Wallowas; hello, Columbia River Gorge! Get ready for your sixth Wonder. The drive down I-84 takes you into the Columbia River Gorge National Scenic Area, which stretches from the Deschutes River in the east to the Sandy River in the west. With the twin ridgelines on either side of the river, the dramatic basalt cliffs and outcroppings stand as a history lesson to how this gorge was formed more than 10,000 years ago by floodwaters from what is now Montana.

On the way, stop for breakfast or lunch in Pendleton at the Rainbow Cafe, which has been serving the public for more than 125 years. Take a detour off the interstate on U.S. 395 to the town of Echo for some wine tasting at Sno Road Winery.

In The Dalles, browse the shelves at Klindt’s Booksellers — the oldest bookstore in Oregon and a great source of Pacific Northwest history, geology and fiction. The Dalles has a growing number of great wineries, too, including Sunshine Mill and Maison de Glace wineries downtown and Dry Hollow Vineyards to the south.

Take the Historic Columbia River Highway west toward the town of Mosier, where you can find more good wineries (like Analemma Wines and Garnier Vineyards at Mayerdale), as well as a cidery/mercantile and cherry and apricot orchards. Mosier is also the eastern end of the Twin Tunnels Trail, a 4.5-mile section of the Historic Columbia River Highway that is closed to automobile traffic,but great fun for walking or biking.

From Mosier, head west on I-84 for five miles to the town of Hood River. Here you can explore the bursting craft-beer and cider scene (at this writing, Hood River had five breweries and nine cideries in operation).

Spend a day exploring Hood River and your sixth Wonder - the Columbia River Gorge. Start with a scenic drive along the Historic Columbia River Highway, stopping at Multnomah Falls and other waterfalls like Horsetail Falls. Enjoy lunch at local favourites like Solstice Wood Fire Pizza or Double Mountain Brewery. In the afternoon, enjoy outdoor activities such as windsurfing, a walk along Waterfront Park, or a visit to a nearby winery or orchard. End your day with a sunset stop at Rowena Crest Viewpoint before enjoying dinner at Riverside or Ferment Brewing Co. for beautiful river views.

Get ready for your seventh and final Wonder: majestic Mt. Hood rising 11,250 feet above sea level. Head south out of Hood River on Highway 35. On a clear day, you’ll see the snowy peak for the entire 40-mile drive. Along the way, stop at a local farm or fruit stand in the Hood River Valley for fresh produce. Continue your drive up to Mount Hood, where you can explore Trillium Lake for a peaceful walk and breathtaking reflections of the mountain. As evening approaches, head to Timberline Lodge for dinner, where you can enjoy a meal with incredible views of the summit.

Your tour ends when you return your rental car to the agreed drop-off point. Alternatively, speak with your Discover North America Travel Specialist about possible trip extensions