5 Scenic Road Trips in Oregon (Itinerary Ideas + Tips!)

Oregon is home to some of the best scenery, people, and activities to explore. The only way to really appreciate everything the area has to offer is to hit the open road and enjoy the sights along the way. Here is a complete list of the best road trips in Oregon, covering everything including cities, small towns, beaches, forests, and deserts.

For those visiting the state, keep in mind that you do not fill your own gas at the station, a worker will come out and do it.

There is also no sales tax, even for non-residences, which is always a wonderful surprise at the register.

Lastly, the weather varies vastly with only a few hours’ drive, dress appropriately depending on your Oregon road trip itinerary.

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Oregon Coastal Road Trip

This road trip up the Oregon Coast is the perfect route for ocean and small-town lovers. Miles and miles of sandy beaches stretch far combined with grassy plains, rock cliffs, and forests.

This Oregon road trip can be done in a few days or a few weeks depending on the number and length of stops.


Whether starting from the south near the California border, at the little town of Brookings, or in the north at the mouth of the Columbia River, follow Hwy 101 the entire way.

The road briefly leaves the coast on occasion to bypass river mouths but will quickly get back to ocean views. Many beautiful and quiet little towns are along the Highway and are worth stopping to stretch your legs and have a look around.

This drive can easily turn into a loop by driving up or down I5 and then exploring the coast. This gives the chance to see some of the larger towns and avoid a repeat drive.

sea lion caves in florence oregon

Sightseeing On This Oregon Road Trip

South Coast

Starting in the south, near the California boarder, popular stopping points include Arch Rock Picnic Area, Prehistoric Gardens, Sea Lion Caves, and the Oregon Coast Historic Railway.

This south bit is more spread out and less crowded, creating a more peaceful and relaxing space to enjoy activities such as sunbathing, kite flying, sandcastle building, and hiking.

Central Coast

Next, the Oregon Sand Dunes National Recreation Area is a must-stop as the sand dunes are beautiful and offer many exciting activities including four-wheeling. Multiple smaller dunes are around on the way to the popular town of Florence.

Other interesting sights including Stonefield Beach, Thor’s Well, and Smelt Sands State Recreation Site are on the way to the larger town of Newport.

yellow lab on sand dunes along a coastal oregon road trip itinerary

North Coast

The northern section of the coast, near the Washington border, boasts larger towns for more shopping and great food. The Devils Punchbowl, a caved-in rock formation, sits before the town of Tillamook.

Famous for its dairy products, stop by for some cheesy eats and ice-cream for dessert.

Cannon Beach, the host of Haystack Rock, is also a must before the charming town of Astoria on the Columbia River and the end of the Oregon coast road trip.

Columbia River Drive Road Trip

This beautiful road trip in Oregon showcases everything the state has to offer as it runs east and west. From the desserts on the east side of the cascades, over the mountains, and then down to the sea there is a little bit of everything to enjoy.


Follow I84 from the little town of Boardman where the freeway meets up with the Columbia River all the way to Portland. After spending a day, or three, in Portland continue along the Columbia River on Hwy 30 until the ocean beaches at Fort Stevens State Park or at Sunset Beach.

Multiple different routes can be taken to get to the coast and detours can add so much more to the road trip experience.

Mount Hood can be added to the trip by taking Hwy 35 and then Hwy 26 to get to Portland. Hwy 14, on the Washington side of the Columbia River, offers a slower but more scenic route to admire Oregon from a distance.

empty highway as seen on one of the best road trips in oregon with mt hood in the background

Sightseeing On This Oregon Road Trip

East Side

Many cute Oregon towns line the Columbia River including Arlington, The Dallas, and Hood River. All of them offering shopping and good food.

Hood River in particular is the perfect spot for some water sporting including windsurfing and kayaking. If you do stop at Mount Hood, there are many wonderful sites and hikes to explore, skiing and snowboarding are also available year-round on its glaciers.

Portland Area

Be sure to stop by the Multnomah Falls, beautiful and large waterfalls right off the freeway, before making your way into Portland.

Known for its fantastic food and hundreds of food carts to enjoy it, this city also has many activities to enjoy including shopping, the Portland Zoo, and vibrant nightlife.

portland oregon skyline from above with mt hood in the back left of the photo

West Side

On the way to the coast, along Hwy 30, you’ll find many more little towns are along this slow and scenic route. Some of the best towns to stop by are Prescott, Westport, and Astoria.

The best food and shopping options are in the slightly larger town of Astoria and since it’s near the coast, seafood is their specialty.

The perfect ending to this road trip is watching the sunset over the ocean at one of the many beautiful sandy beaches nearby.

astoria oregon with winding road in the foreground

Small Town Road Trip in Oregon

This road trip loops around the east side of Oregon, the desert side. The sun is much more likely to be present and warm in the spring and summer.

Also, this is the perfect spot for wine lovers as this is prime wine country that is best explored by the hundreds of tasting rooms scattered all around the country side. Beautiful and peaceful forests as the backdrop make this a perfect relaxing getaway.


The starting city for this road trip is in Ontario, Oregon, right on the border of Idaho though the loop can be started and ended at any point and in either direction.

From Ontario, take Hwy 26 to Hwy 20 and follow that all the way across the wide-open desert to the popular tourist stop of Bend.

From there, turn north onto Hwy 97 until you hit the Columbia River. Turn back east onto I84 and follow it through La Grande all the way back to the starting city of Ontario.

This Oregon road trip has the added appeal of countless other route and roads to truly make the trip your own.

To make the trip longer, shorter, or to hit desired parks or towns there is no way to go wrong whichever path is chosen. Hwy 26 from Ontario to Redmond is a popular choice as it passes many charming towns along the way.

red barn near la grange oregon with mount hood in the background, a great sight along one of the best road trips in oregon

Sightseeing On This Oregon Road Trip


The two largest towns on this loop is Bend and Ontario, both of these have the most options for shopping and familiar foods.

Many fun tours depart into the area from these towns including white water rafting, biking, hiking, canoeing, and skiing.

Read our guide to the best things to do in Bend!

two hikers near bend oregon

Small Towns

The small towns in between, dotted all along the route, are what makes this road trip truly unique. Local wineries, farm-to-table dining, and art is available everywhere.

Some of the more popular small towns on this Oregon road trip itinerary are Vale, Burns, Arlington, Pendleton, and Baker City.


Some fun detours to add to the road trip put on many more miles but is well worth it for more peace and breathtaking beauty.

Multiple national forests are in the area including the Wallowa-Whitman National Forest, the sight of the deepest gorge in North America.

Charming towns off the beaten trail including Enterprise and Paulina offer local yearly events and more to explore.

river running through national forest on oregon road trip

I5 Corridor

From Medford through Eugene and all the way to Portland, this is the best way to experience diversity and a great nightlife.

Between the cities, the beautiful forests and farmlands are a good breather from the hustle and bustle of people.


As the name suggests, this route up or down the major freeway of I5 hits all the cities in Oregon.

I5 runs only north and south, to make a trip that doesn’t have repeat roads, the coastal Hwy 101 or the mountainous Hwy 97 are great options. Both will create a loop starting from the border near Washington or California.

Sightseeing On This Oregon Road Trip

South End

The smaller cities of Medford, Grants Pass, and Roseburg and everything in between is a relaxing way to start this fantastic road trip with antique shopping and many parks to enjoy.

Crater Lake National Park is a bit further east off I5 in this area, but well worth the extra miles.

overview of crater lake np


Multiple small and charming towns line the road to Eugene, the next city. But if you have time for one, stop by Cottage Grove as it has the most beautiful display of covered bridges west of the Mississippi River.

Further on to Albany and Salem, good shopping, food, and beautiful parks await visitors.

North Side

The last stop before hitting Washington State over the Columbia River is Portland.

It is easy to spend a few days here as there is so much to do like walking along the waterfront, eating world-class food, and spending time at Powell’s City of Books. Night clubs, events, and bars are also often available well into the night.

multnomah falls near portland oregon

The Ultimate Oregon Loop

The road trips covered previously gets to nearly every nook and cranny of the beautiful Oregon state.

This ultimate Oregon road trip combines everything wonderful about the state and all of the different sceneries to enjoy. Any combination of these roads can be used to make a perfect combination for your purposes.


The trip recommended here is to start in Portland and head east along the Columbia River on Hwy 84 following it all the way to Ontario near the Idaho border.

Then, turn back west and take one of many highways to make it to Bend. Hwy 97 south will take you to near Crater Lake, a must-do when visiting Oregon. Keep going west by one of the smaller highways to get to the coast.

Lastly, end the road trip by traveling north along Hwy 101.

moody light on an oregon road trip through a forest with some fall foliage

Sightseeing On This Oregon Road Trip


Near Hood River, be sure to stop by Fruit Loop, a stretch of road where vendors set up stands to sell local produce, the perfect place to stock up on snacks. The many little towns along this route are great places to stop for some shopping and food. Charming bed and breakfasts can be found all over.

After the town of Ontario, more small towns dot any of the routes chosen back west. Yearly events here including rodeos and concerts can be attended.

These along with local art and food make a relaxing trip with a beautiful desert backdrop. Don’t forget to stop by the many National Forests where hiking, biking, bird watching, and many other outdoor activities are available.


Bend allows many more options for outdoor activities as it is a popular outdoor getaway.

From skiing, snowshoeing, and dog sleighing in the winter to white water rafting, canoeing, fishing, and mountain biking in the summer there are endless possibilities.

A few hours south in Crater Lake, hiking and swimming are available in the magnificent park along with many great photo opportunities.


Along the coast, miles of beaches for enjoyment by hiking, sand castle building, wildlife observing, and swimming. The little towns have many antique shops and good food to stop for a stretch of the legs.

Be sure to stop by the beautiful Oregon Dunes for an exciting day of four-wheeling on sand dunes. The town of Tillamook is home to the famous dairy factory, the perfect spot for lunch and dessert.

Hay Stack Rock located on Cannon Beach is also one of the best places to stop on an Oregon road trip for photos and to observe tidepool wildlife.

Be sure to bring clothes for warm, sunny days and for wet, cold days as the weather on the coast can vary quite a bit day to day.

2 photos of oregon, one of mount hood and one of cannon beach, black and red text on a white background reads "5 best road trips oregon"