Oregon road trip: 2 and 3 week itinerary

Oregon is one of the most versatile states in the USA and a perfect destination for a road trip. These are the best itineraries for an Oregon road trip.

Why do you want to go road tripping in Oregon?

Oregon, located in the northwest USA, is a wonderful destination for an epic road trip. With its diverse landscapes, from rugged coastlines to snow-capped volcanoes and dark forests filled with waterfalls, Oregon is a wonderfully versatile destination. Thereby, it is also not nearly as crowded (yet) as in the Southwest.

I drove around the northwestern USA for over a month, spending much time in beautiful Oregon. In this blog, I’ll share an overview of great places to visit in Oregon and two fun routes for a road trip. An itinerary for a 2-week round trip and one for 3 weeks, including a day-by-day schedule.

The most beautiful places in Oregon

Before I share the itineraries with you, let me tell you the highlights of Oregon.

1. Portland: Oregon’s largest city is known for its vibrant food and drink culture, green parks, and eclectic atmosphere.
2. Columbia River Gorge: This spectacular area is home to numerous waterfalls, including the iconic Multnomah Falls.
3. Mount Hood: Oregon’s highest mountain where you can hike, ski, and do other fun outdoor activities.
4. Cannon Beach: This quaint coastal town is known for its long sandy beaches and the iconic Haystack Rock.
5. Crater Lake National Park: This national park houses the deepest lake in the U.S., created by a volcanic eruption thousands of years ago.
6. Bend: This vibrant city in central Oregon is an outdoorsman’s paradise, with opportunities for hiking, biking, rafting, and more.

Discover more beautiful places? Read Exploring Oregon: 10 beautiful places to visit.

Oregon road trip: 2 week itinerary

What does an Oregon road trip look like? Let’s start with an itinerary for two weeks.

Day 1 & 2: Portland

Your Oregon tour starts in Portland, which is the state’s largest city. Portland has many great attractions, including the famous Powell’s City of Books bookstore, the Shanghai Tunnels, and Pittock Mansion. The city is also known for its food and drink culture, for example, you can get the tastiest donuts in America here.

• Hotel Tip: The Hotel Zags Portland (4⭐) – Beautiful colorful boutique hotel in a very central location. The museum features as many as 500 works of art by local artists.
• Fun thing to do: Discover the best spots in Portland on a bike tour accompanied by a local guide.

Day 3 & 4: Columbia River Gorge

• Mileage: 70 kilometers (to Cascade Locks).
• Travel time: 45 minutes

Portland is surrounded by nature, so you don’t have a long drive today. Drive east to the Columbia River Gorge. With Cascade Locks as a base, you can very easily visit the most beautiful places in the Columbia River Gorge.

Along the river, you can see an awful lot of waterfalls, the most famous of which is Multnomah Falls. There are several state parks you can visit, such as Lang State Park, Starvation Creek State Park, and Memaloose State Park. All of these parks are bursting with beautiful hiking trails and waterfalls.

• Hotel tip: Best Western Plus Columbia River Inn (3⭐) – One of the best rated hotels in Cascade Locks. From the hotel, you can walk right into the forest. Breakfast included.

Day 5 & 6: Mound Hood

• Number of kilometers: 90 kilometers
• Travel time: 1 hour and 15 minutes

During an Oregon road trip, you can’t avoid Mount Hood. This stratovolcano dominates the landscape and is Oregon’s highest point at 3,429 feet. Several ski resorts surround Mount Hood, making it a special destination in winter.

The rest of the year you can hike and bike to your heart’s content in Mount Hood National Forest. Enjoy the beautiful views, discover (more) waterfalls and admire the often snow-capped volcano. At the foot of Mount Hood, you will find the Timberline Lodge. This famous 1930s hotel was the filming location for the hotel in The Shining.

• Hotel tip: Timberline Lodge (3⭐) – The most iconic hotel in Oregon.

Day 7 & 8: Bend

• Mileage: 185
• Travel time: 2 hours and 30 minutes

After a few days in nature, it’s time to head back to a city, although Bend is also a very adventurous destination for outdoor enthusiasts. The city itself has a very cozy center and is known for its many beer breweries.

In addition, Bend is a good base for a scenic bike ride, a rafting adventure on the Deschutes River or a scenic canoe trip. A visit to the High Desert Museum is also a must, here you will learn more about Oregon’s history and culture.

• Hotel tip: Oxford Hotel Bend (4⭐) – A beautiful boutique hotel in the middle of the cozy downtown area.
• Fun thing to do: Join a canoe trip and enjoy the beautiful views of several volcanoes. During a break, enjoy locally brewed beers.

Day 9 & 10: Crater Lake National Park

• Number of kilometers: 200 kilometers
• Travel time: 2 hours and 30 minutes

Today you will travel to one of the most beautiful places in Oregon: Crater Lake National Park. Crater Lake is a deep blue lake in the caldera of an extinct volcano, Mount Mazama. The lake is nearly 600 meters deep in places, making it the deepest lake in the United States of America. The crater rim is surrounded by beautiful mountain landscapes, with steep cliffs, dense forests and snow peaks.

A beautiful area for hiking or biking and in the process you can also take a boat ride on the lake. You can also spot wildlife here; for example, I saw two bears during my visit!

• Hotel tip: Aspen Inn – Cozy motel in Fort Klamath. It may look a little corny, but it fits right in with the atmosphere of an American road trip, and it is highly rated.

Day 11, 12 & 13: Oregon coast

• Mileage: 285 kilometers (to Newport)
• Travel time: 3 hours and 35 minutes

Feel like getting a breath of fresh air? That’s convenient because for the next few days you’ll be exploring Oregon’s beautiful coast. Drive to the coast and spend time in Cannon Beach. Explore the beaches, visit Haystack Rock and enjoy the sunset.

You can choose to sleep in a different place each night or choose one place as a base (Newport or Cannon Beach, for example). Beautiful places to visit include at least Coos Bay, Newport, Cape Lookout State Park, and Cannon Beach with the iconic Haystack Rock.

• Hotel tip: Inn at Nye Beach (3⭐) – Fine hotel on the beach in Newport. Breakfast included.

Day 14: Back in Portland

• Mileage: 300 kilometers (from Newport via Cannon Beach)
• Travel time: 4 hours

After a wonderful 2-week tour of Oregon, you will return to Portland for your flight home. You may still have time for a last-minute exploration of the city. Enjoying the memory of this unforgettable trip!

Map 2 week Oregon road trip

This is an image of the map. Click here to zoom in.

Total length: 870 miles (1400 kilometers) + additional miles to sights just off the route.

Oregon road trip: 3 weeks

Do you have three weeks to explore Oregon? That’s great, because then you can explore more beautiful places in this state and slow down a bit.

For the three-week route, keep most of the same stops as the two-week roundtrip, only you’ll have more time in some places and also visit the beautiful John Day Fossil Beds National Monument. This is a fun itinerary for 3 weeks in Oregon.

Day 1 – 3 Portland – Starting in Portland, explore the city extensively and possibly take a day trip to the Willamette Valley for wine tastings.

Day 4 and 5 Mount Hood – Explore Mount Hood and the surrounding areas, with opportunities for longer hikes or other outdoor activities.

Day 6-8 Columbia River Gorge – Visit the Columbia River Gorge and spend more time hiking and exploring the waterfalls and viewpoints.

Tip! Cottonwood Canyon State Park is a nice stop between the Columbia River Gorge and John Day Fossil Beds.

Day 9 to 10 John Day Fossil Beds National Monument – Explore the three sections of John Day Fossil Beds National Monument. Walk among green rocks in the Sheep Rock District and explore the red rolling hills in the Painted Hills District.

• Accommodation tip: There are few lodging options in the region, but Spok’n Hostel in Mitchell is undoubtedly one of the best. This little white church converted into a hostel. In addition to a multi-bed dormitory, they also have a number of private rooms. Toilets and showers are shared.

Day 11, 12 & 13 Bend – Head to Bend and enjoy the many outdoor activities, such as hiking at Smith Rock State Park or visiting the volcanic caves of Newberry National Volcanic Monument.

Day 14 & 15 Crater Lake National Park – Visit Crater Lake National Park and explore the area extensively, by hiking or taking a boat ride.

Day 16 Eugene – The city of Eugene is another nice stop before exploring the Oregon coast. The city is best known for the University of Oregon, and because of this there is a pleasant atmosphere downtown. You’ll find plenty of restaurants, bars, breweries and stores. And even if your trip prefers nature, Eugene is fun to visit because again, you can do some great hiking, biking and kayaking.

• Hotel tip: The Campbell House Inn – Cozy small accommodation with a garden. It is located among several parks and within walking distance of downtown.

Day 17 – 20 Oregon Coast – Travel to the coast and spend time in Cannon Beach and nearby coastal towns such as Astoria and Tillamook.

Day 21 Portland – Travel back to Portland to conclude your trip.

Map 3 week Oregon road trip

This is an image, click here to zoom in.

• Length of the 3 week itinerary: approximately 1060 miles (1700 kilometers)

Tips for your Oregon road trip

A few final tips for your Oregon road trip.

• Oregon has a temperate climate, but be prepared for variable weather conditions, especially on the coast and in the mountains.
• Book accommodations in advance, especially during peak season (June-August) and in popular areas such as Portland and the coast.
• Oregon is known for its craft beer, wine, and food. Visit a brewery regularly to sample local beers and eat the tastiest seafood on the coast.
• Respect nature and follow the principles of Leave No Trace to preserve Oregon’s beautiful landscapes for future generations.

Whether you opt for a 2-week or 3-week roundtrip, Oregon offers an unforgettable experience with its diverse landscapes, numerous outdoor activities, and cozy cities. With these itineraries and tips, you’ll be ready for an adventure in the beautiful Pacific Northwest.

Book your trip to Oregon

Are you excited to explore Oregon after reading this article? Book your trip now!

✈️ Plane tickets – Portland has the largest airport in the state. Check WayAway to find the best deals and cashback on plane tickets.

🚘 Rental car – For an epic road trip, you obviously need to have a rental car. Check Rental Cars to find the best deals.

💊Travel insurance – Having good travel insurance will give you peace of mind. Check Insubuy to find the best travel insurance that fits your needs.

🎡 Tours and Activities – There are tons of fun tours and activities to do in Oregon! Check Get Your Guide for all options.

Read more about Oregon and Northwest USA

Are you curious about Oregon and America’s Pacific Northwest? These travel guides are full of tips:

Moon Oregon: Coastal Getaways, Craft Beer & Wine, Hiking & Camping

Lonely Planet Best Road Trips Pacific Northwest

In addition, you can also read a lot on this website about traveling in the USA as I spent a lot of time road tripping and hiking in the United States.

• National parks in Oregon and Washington: explore the Pacific Northwest
• Portland to Yellowstone road trip: amazing 4-week itinerary
• Blue Basin Overlook Trail: a beautiful hike in Oregon

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