Road Trip in Oregon: The Ultimate Itinerary

Crater Lake in Oregon at sunset. A MiscGyan image from a road trip in oregon.
Picture of Rachit Jawa

Rachit Jawa

Oregon holds innumerable treasures in its chest. Some are popular tourist destinations while others are tucked away on an off-beat path. Oregon is blessed with some spectacular terrains showcasing the diversity of elements nature has to offer. From the sandy beaches with cool waters to the mountains with views that will make your day, and the deserts with painted slopes, Oregon has it all. Read on for a perfectly curated three-day road trip to South Oregon. This is relaxing, explorative, and efficient all at once. An Oregon road trip itinerary to trip on!

One of the biggest perks of living in Portland, Oregon is the never-ending list of drivable destinations that are perfect for a weekend getaway. And the drive, no matter which direction you are headed, is sure to be a delight. This particular Oregon road trip is ideal for any long weekend between the months of April-October. Winter months may need carrying traction tires or chains as the roads get snowy at higher altitudes.

Day 1: Sunriver, Oregon

We started on a Friday evening after work. All our road trips start with cappuccinos to-go and banter about work but we quickly progress onto deep psychological and existential discussions. The Oregon countryside scenery is the perfect accessory to that. A charming three-hour drive took us to the stunning Sunriver Resort. This was our cozy home for the weekend and had the perfect cabin vibe. Sunriver, OR is a quiet town with log cabins and lakes that you can bike along, bustling in the summer as a popular destination for families. It is conveniently located mid-way to the two destinations we intended to visit, Crater Lake National Park and Painted Hills.

Pro tip: Beat the crowds at both of these destinations by going right before summer.

oregon road trip

Life is better at the cabin! Sunriver Resort, Oregon

Day 2: Crater Lake National Park, Oregon

Next morning was made sweeter by a rather satisfying brunch at an amazing local cafe, Cafe Sintra, we started our drive to the Crater Lake National Park. Three hours of picturesque drive and we reached the beautiful lake. Be prepared that the first look will take you aback. A daunting volcano that sunk into a deep crater that filled with water overtime to create this lake. It was so blue and clear that it made me pinch myself. The edges were filled with snow but the sunshine made it warm and comfortable. We went to a few different viewpoints, all drop dead gorgeous! The view pictured below is just a short walk away from the visitor center.

oregon road trip

As we started to head back, the sun was about to set. The sunset in our rearview mirror looked so gorgeous that we decided to make a U-turn and head back to the lake! Skies painted with a peachy glow upon the mirror-like sheet of water. I will never forget that view and how it made me feel. 

Day 3: Painted Hills, Oregon

Fuel for the day

Next morning’s breakfast destination was the sunny patio at McKay Cottage Restaurant in Bend, OR. Bend is a town in central Oregon, only a few minutes away from the Sunriver resort, and is on the way to the splendid and artful, Painted Hills. Bellies full, hopped up on coffee, we drove towards this place, rightfully called one of the seven wonders of Oregon.

These hills are a part of the John Day National Monument. They not only contain fossils, but also secrets of long-term evolution of the area. The most interesting part of the drive was when we began to see colorful streaks in the lofty dusty mountains. This place has an extra-terrestrial appearance. It makes you feel like you stepped on another planet. See the pictures below and decide for yourself. 

oregon road trip

 Unearthly views at Painted Hills, Oregon

oregon road trip

Did we just land on Mars? Painted Hills, Oregon

The Road Back Home

The breakfast on the third morning was at Jackson’s corner in Bend, OR. You don’t want to miss this place. Their avocado toast was great but the unique lattes were an absolute delight. It will be difficult to decide what to get with so many amazing options, so don’t be shy to get a second latte for the road! 

Local Tip: Don’t miss Jackson’s Corner cafe in Bend, OR for their amazing lattes. Golden milk and lavender latte were our favorites!

With the driving spilled over into multiple days, the road trip felt comfortable and effortless. We drove back home with our hearts full, and pumped to plan the next road trip. DM us on Instagram to share how you like your road trips to be. Packed with activities by the hour or more relaxed and vacation-like? Also, tell us your favorite road trip destination (Oregon or elsewhere 😛 ) and who would you like to do it with? We are happy to answer any specific questions you might have about visiting one of these places. Happy road tripping!

You can catch more on our travels via our blog. Don’t forget to follow us on Instagram for a regular pinch of joy. Cheers!


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