7 Best Oregon Road Trips

Fancy exploring the Beaver State? An Oregon road trip offers a world of unique sights, scenic parks and historic cities for you to uncover.

If you’re into film, TV and music, you need to take the Pop Culture Cruisin’ trip to hotspots that inspired iconic shows like the Simpsons and The Lost Boys. If you are into the wacky, mysterious and eccentric, head out on the Weird, Weird West trip to discover some truly peculiar attractions like the Atomic Survival Town and Mount Tabor in Portland.

Our American Road Trip Planner has fantastic routes for every interest and occasion. Check out our favorite Oregon road trip stops below to start planning your next adventure.

Missouri to Oregon: The Oregon Trail

2064 miles, 14 days, 13 stops

Follow the trail of those who went before us and take in the 19^th century explorers’ route as they headed from Missouri to Oregon in search of a new place to settle. Luckily, our guide has everything all worked out, meaning you’ll have less trouble getting from A to B than the pioneers did.

When you arrive in Oregon, head to the Oregon Trail Interpretive Center and look into the history of the settlers, explore an old gold mine and enjoy plenty of tours and exhibits. One of your last stops will be at the Pittock Mansion, whose owners were important in the community of Portland and helped many people with jobs and local charities. 

Follow the Oregon Trail road trip

Portland to Rogue River-Siskiyou National Forest: Summer on the Oregon Coast 

639 miles, 5-7 days, 10 stops

Travel down the stunning west coast of America using Highway 101 and take in miles and miles of ocean on one side and mountain ranges on the other. Marvel at amazing sights on a trip you’ll never forget.

Start in Portland, the largest city in Oregon, famous for spectacular mountains and the Willamette River. Follow the Columbia River to Astoria – Oregon’s oldest city – where you can go seal spotting and sample local seafood.

Then begins your journey south through Ecola State Park and Cannon Beach, continuing on to the Siuslaw National Forest. Take in the breathtaking scenery of beautiful bays and rugged coastline, before stopping the tour at Rogue River-Siskiyou National Forest. 

Enjoy Summer on the Oregon Coast

Washington to California: Pacific Coast Paradise 

1431 miles, 10 days, 14 stops

If you fancy an authentic American adventure, look no further than this Pacific Coast road trip – filled with spectacular scenery and breathtaking attractions.

From the starting point in Washington, you’ll head to Oregon and take in the Oregon Museum of Science and Industry. This is ideal for families who want to try the hundreds of interactive displays and conduct experiments.

From there, head to Mount Hood and admire beautiful views of the gigantic snow-topped volcano that dominates the horizon. It is well worth a trip, and you can enjoy various sports while there.

Plan your Pacific Coast Paradise adventure

Arizona to Oregon: Into the Valleys

1764 miles, 14 days, 12 stops

Travel through some of the most famous valleys of the west coast, with perfectly placed stops for a hike along the picturesque trails. Traverse Death Valley, the Grand Canyon and Yosemite National Park.

See the breathtaking Thor’s Well (Cape Perpetua) and Crater Lake Natural Park as you pass through Oregon on your road trip. Crater Lake has some of the purest water in the world and looks beautiful in all seasons.

This trip deserves nothing less than a convertible, so pick one from our range of Ford Mustang GTs and Chevrolet Camaros. 

Venture into the Valleys

Washington to California: Pop Culture Cruisin’ 

1363 miles, 10 days, 13 stops

Want to see some of the most famous pop culture references of the last few decades? Look no further than the Pop Culture Cruisin’ road trip, which covers a variety of music, TV and film references.

In Washington, start your trip at the Kurt Cobain Memorial Park to discover the Nirvana frontman’s hometown and learn about his early influences. Take the highway south to visit the Goonies house in Astoria, Oregon – yes, it’s still standing after being saved from demolition in the 80s classic.

Oregon is also home to the location that inspired one of the most famous opening sequences in TV history. The Simpsons’ Springfield is based on the real Springfield in the state. See how many Simpsons’ references you can find throughout the town, including a Moe’s Tavern. 

Discover Oregon’s best pop culture references

Washington to Nevada: The Weird, Weird West

1950 miles, 14 days, 13 stops

America has a history with the weird and wacky, and the west coast has more than its fair share of quirky spots to see. Pack up your rental with everything you’ll need to take on a few mysteries and head out to the starting point at Gas Works Park in Seattle, WA.

From there, you’ll head down to Portland. Visit Ye Olde Curiosity Shop, where you’ll see Sylvester the mummy and browse several items covering many different cultures from the last 100 years. View Mount Tabor and see this urban volcano in all its glory. Play basketball or tennis at the summit and look out over the city below.

You’ll then uncover some of California’s quirks, before ending up in Nevada at the Atomic Survival Town and Clown Motel. 

Find out how weird the west coast can be

Hollywood to Seattle: Eat the West Coast

1446 miles, 7-9 days, 12 stops

The best way to anyone’s heart is through their stomach, or so the saying goes. As luck would have it, there’s a road trip that will get you tasting a delectable array of dishes from celebrity hangouts in Hollywood to street food in Seattle.

As you pass through Oregon, enjoy fantastic eateries like SweetWaters on the River, where you can get American Classics and relax as you look out over the Willamette River. Just off the main highway in Portland, head to Higgins for fine dining in an understated atmosphere, serving up seafood classics, creamy risotto and wonderful beef brisket. 

Eat the West Coast

Ready to take in the sights and sounds of the Beaver State? Reserve your Oregon car rental with Hertz for peace of mind on your next road trip.

Check out the Hertz blog for more travel tips and inspiration.