The Ultimate Oregon Road Trip Itinerary

October 7 2021, 11:39pm

Pack your bags and get ready for an unforgettable road trip to Oregon! Oregon is a gem in the Pacific Northeast region that will quickly become your favorite state to visit.

Our Oregon road trip itinerary will take you to all of the most iconic parts of the state. You’ll ride along the famous Oregon Coast Highway, climb to the top of Mount Hood, and go for a refreshing swim in Crater Lake.

There is beautiful scenery along the entire trip, which makes you a true believer in the phrase, “enjoy the journey.”

Let’s check out the best Oregon road trip ideas.

portland oregon neon sign

Portland to Hood River – approximately 62 miles

The first leg of our road trip takes us from Portland to Hood River. You’ll start the journey in Portland, Oregon’s largest city, so it’s the perfect base to explore the city’s attractions before heading out onto the road surrounded by scenic natural sights.

Portland to Hood River is only 62 miles in distance, but there are plenty of cool things to see along the way that’s definitely worth a stop.

Portland

Take advantage of being in Portland to check out its thriving culture, art, and food scenes. Washington Park is a large urban park where you can go for a leisure walk through the Japanese Garden or see the animals in the Oregon Zoo. Stop by the Portland Art Museum, one of the oldest museums in the US, to see its vast collection of Native American, Asian, and contemporary art. And don’t forget to pick up a few Oregon travel guidebooks from Powell’s City of Books – the largest bookstore in the world.

When you’re ready, hop on I-84 and head east to your next stop.

oregon waterfall

Waterfalls Galore

You’ll soon realize that driving through Oregon will take you to some impressive natural landmarks. Unfortunately, it will take forever to take pictures of them all, so we’ll give you the best ones to check out.

This route takes you through the Columbia River Gorge, where you’ll encounter tons of scenic waterfalls. The famous waterfalls along this route are Bridal Veil Falls, Melaka Falls, Wahclella Falls, Tunnel Falls, and of course Multnomah Falls.

Columbia River Gorge National Scenic Area

The Columbia River Gorge runs along the Oregon-Washington border. The entire drive along the highway offers spectacular views of the gorge. You’ll reach the national scenic area as you near Hood River, where you’ll find tons of hiking trails that take you to awesome viewpoints.

Views looking into the gorge are breathtaking as you see the Columbia River flowing 4,000 feet below in the canyon.

mt hood

Hood River to Bend – approximately 145 miles

The second leg of the road trip between Hood River and Bend is one of the most scenic parts of the Oregon road trip. You won’t believe how many different types of landscapes you’ll pass along the way.

Get your cameras and hiking boots ready to embark on the scenic drive to Bend.

Mt. Hood National Forest

As you drive, you’ll see the snow-capped peak of Mt. Hood emerging over the horizon. It’s an active volcano and the highest peak in Oregon. The area surrounding the volcano is designated as the Mt. Hood National Forest.

Since Mt. Hood is nearly considered dormant and showing no signs of erupting anytime soon, feel free to venture out and explore the peaks! There are many miles of trails that extend along the base or take you up to the summit. 

Be sure to take in the sights from the ground and peak.

Warm Springs Indian Reservation

You’ll get to experience one of Oregon’s largest Indian Reservations—Warm Springs Indian Reservation. It’s one of the unique places to visit in Oregon for your road trip itinerary.

The land is owned by the Confederated Tribes of Warm Springs, who are more than welcoming to visitors. Check out the Museum at Warm Springs to learn more about the tribes’ history. And if you’re looking to relax after the long hikes at Mt. Hood, visit the natural hot springs at Kah-Nee-Ta resort and Spa.

smith rock

Smith Rock State Park

Ready to see some unique rock formations? The route leads you directly to Smith Rock State Park. It’s part of the High Desert, which sits nearly 3,000 feet above sea level. You’ll find some of the best hiking trails in Oregon.

If you have time, we recommend going for a trek on the popular Misery Ridge and River Trail, which takes you along the canyon, where you’ll find caves, rock formations, and more. Or, if you prefer to stay in your car, the Burma Road Loop is an excellent alternative.

Bend to Medford – approximately 170 miles

Most people traveling between Bend to Medford tend to fly, but they don’t know what they’re missing. That’s why we’ve included this leg in the journey for your road trip so that you can check out the iconic landmarks.

The journey takes you alongside the Cascade Mountain range, where you’ll pass several notable peaks. We’ve included a few stops at the famous locations along this 170 mile leg.

Newberry National Volcanic Monument

One of the top things to do in Bend is visiting the Newberry National Volcanic Monument. The park consists of the Newberry Volcano and the Deschutes National Forest—two fascinating places to visit in Oregon for nature-lovers.

Within the park, you’ll find plenty of hikes, viewpoints, and seeing wildlife. Also, be sure to check out the lava flows and the volcanic vents. You can also hike the Paulina Peak trail to reach the highest point at nearly 8,000 foot elevation!

crater lake

Crater Lake National Park

The next stop takes you high into the Cascade Mountain Range, where you’ll have scenic views as you drive through the mountain passes. Crater Lake National Park is a bucket list destination and one of the most beautiful sights you’ll see on your Oregon road trip.

As the name suggests, Crater Lake was formed in the crater of Mount Mazama. It’s the deepest lake in the US, where you’ll literally be descending into the mouth of a former volcano.

Crater Lake is a place for recreation and sightseeing. It’s open to the public for swimming or a boat tour to Wizard Island, located in the center of the lake. In addition, there are hiking trails around the lake for stunning views of the crater.

Wineries

Medford, OR, is a popular wine region destination. The landscape and weather conditions are perfect for cultivating the best grapes for wine production. Make a stop in Medford to check out the local wineries and taste the savory flavors of the region.

Popular winery destinations in Medford are RoxyAnn Winery, EdenVale Winery, and the DANCIN Vineyards. Each of these places offers wine tasting and tours of the grounds to see how it’s produced.

medford oregon
Photo by as737700

Medford to Eugene – approximately 165 miles

Hope you enjoyed the drive through the mountains because this leg of your road trip in Oregon gives you a break from the peak-lined scenery. Traveling from Medford to Eugene is a 165 mile trip on the I-5 highway that you’ll have a lot of fun exploring Oregon’s wildlife and cultural heritage.

Valley of the Rogue State Park

The first must-visit stop along the journey is at the Valley of the Rogue State Park. It’s hard to avoid since you’ll run right into it soon after leaving Medford. This popular state park has several natural landmarks and outdoor recreation.

The centerpiece of the Valley of the Rogue State Park is the Rouge River. There are hiking trails leading through the river valley or get overlook views from the cliffs above it. It has designated camping grounds available if you want to stay overnight.

Wildlife Safari

You had a chance to check out the wildlife at the Oregon Zoo in Portland, but in case you skip it, there’s another place that’s just as good! The Wildlife Safari is located in Winston, Oregon that offers an immersive experience with the animals.

At Wildlife Safari, you’ll drive through the park’s 615 acres, where the animals roam freely. It has hundreds of different species, including cheetahs, elephants, pandas, giraffes, lions, and rhinos. It takes about an hour and a half to drive through it, and there are also walk-through exhibits.

University of Oregon Campus

The University of Oregon is home to the Oregon Duck—one of the top things to do in Eugene, Oregon! If you’re lucky, you’ll get a chance to see one of the collegiate games—it’s a major university of football and basketball. The entire athletic program is sponsored by Nike, headquartered nearby, so it has arguably the best jerseys and stadiums.

If you’re not into sports, the university is also a hub for local art and culture. Two prominent cultural venues are located on the campus—the Jordan Schnitzer Museum of Art and the Museum of Natural and Cultural History.

eugene oregon
Photo by lulek

Eugene to the Oregon Coast – approximately 70 miles

What’s an Oregon road trip without a trip on the iconic Oregon Coast Highway? The Oregon coast trip ranks as one of the most scenic highway road trips in the US. People travel from all around the country just to drive this leg of the road trip.

Starting your trip in Eugene means that you’ll only be about an hour’s drive away from the coast. The entire Oregon Coast Highway stretches over 360 miles along the Pacific coastline, but save that route for another journey because the stops you’ll see heading north are more than enough to make you want to return and see it all.

Heceta Head Lighthouse State Scenic Viewpoint

After you’ve finished enjoying all of the fun things to do in Eugene, Oregon, make your way to the Oregon coast. Hold your anticipation from stopping before reaching the coast because you’ll want to maximize your time there. The Heceta Head Lighthouse State Scenic Viewpoint will be your welcome to the coast.

Heceta Head Lighthouse State Scenic Viewpoint is home to the famous Heceta Head Lighthouse. The scenery surrounding the 205 foot tall lighthouse perched on the cliffside is one of the most picturesque things you’ll see on the trip. It was built in the 19th century and is Oregon’s strongest light, visible up to 21 nautical miles.

Don’t forget to check out the nearby Sea Lion caves. You can take a guided tour through the sea lions’ natural habitat.

Natural Landmarks

One of the unique things about the Oregon coast trip is seeing all of the unique natural landmarks formed by erosion. Two of the must-see sights are Thor’s Well and the Devil’s Punchbowl.

Each of these areas has observation decks and nearby parking so that you can get out and see the sights. But, of course, the experience at each spot is dependent on the water conditions to get the full effect!

depoe bay

Depoe Bay

About halfway up the Oregon Coast (on this route), you’ll reach the small town of Depoe Bay. It’s a great place to refuel and see one of its most famed residents—whales.

Depoe Bay is a popular whale-watching town in Oregon since it’s located right along the path of the migratory whale route. There are so many whales that you can easily stand on the coast and spot them as they swim to the surface. There are also boat tours that get you up close and personal to the giant mammals.

Oregon Coast to Portland – approximately 80 miles

It’s not hard to see why the Oregon Coast is one of the favorite parts of any Oregon road trip itinerary. Lucky for you, this leg of the trip is designed to give you one last look at the beautiful coast before heading back inland to Portland.

Portland is about an hour and a half away from the coast. There are a few other things you’ll want to stop by before returning home.

cannon beach

Cannon Beach

Cannon Beach is one of the most photographed locations on the Oregon Coast trip, thanks to Haystack Rock. This towering landmark has been flooding Instagram feeds ever since it was first photographed, and now it’s a major tourist destination.

Get there early because there are always people at the beach to see the rock. It’s a 235 foot tall rock protruding from the ocean. It’s an excellent spot to take pictures of the sunrise, sunset, and anytime in between. The beach is also fun to enjoy when the weather is nice.

River Northwest Museum of Rocks & Minerals

You’ve spent a lot of time exploring the natural rock formations throughout the road trip. Well, now, it’s time to learn more about them. Visit the River Northwest Museum of Rocks & Minerals to see one of the largest museums of its kind.

River Northwest Museum of Rocks is listed on the National Register of Historic Places and affiliated with the Smithsonian. Its small personal collection of rocks has grown into a collection of more than 20,000 objects.

Take a guided tour of the museum to learn about the fossils, meteorites, minerals, and petrified wood on display.

nike world headquarters

Nike World Headquarters

You can’t visit Oregon without paying a visit to the Nike World Headquarters—but we have good news and bad news. The bad news (everyone prefers bad first) is that it’s a closed campus and doesn’t allow visitors. The good news is that you can still check out one of the buildings on the campus—Prefontaine Hall.

Prefontaine Hall is a small exhibition museum showing the history of Nike and several collectible items like jerseys and shoes. If you’re a Nike fan, you’ll feel right at home.


Are you convinced yet that an Oregon road trip should be the next on your travel bucket list? Well, you’re not alone! This road trip is perfect in any season, and these Oregon road trip ideas have a mix of activities and sights for everyone to enjoy. So, whether you’re a culture-junkie or a nature-lover, you’ll have plenty to keep you busy during the trip.

Let me know in the comments what part of the road trip you’re most excited about seeing!

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