Kessi World

Mindful travel around the Pacific Northwest.

Oregon road trip — photo gallery and helpful tips

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Oregon road trip — Table of Contents

  • Photo Gallery — diverse terrain
  • Key regions of Oregon (coming soon)
  • Itinerary ideas (coming soon)
  • Interactive Map
  • Helpful tips (coming soon)
  • Planning guide (coming soon)
  • How to get to Oregon (coming soon)
  • Vehicles (coming soon)
  • Food (coming soon)
  • Where to stay (coming soon)
  • Resources (coming soon)

Oregon road trip — photo gallery of a 1,500-mile drive around the Beaver State

I grew up in Oregon and spent my formative adult years living in Portland. My friends and I took many trips to Central and Eastern Oregon, including Joseph and Bend. I even made day-trips to now defunct Kah-Nee-Ta on the Warm Springs Reservation. In my life working in sales covering the Oregon region for Alaska Airlines, I drove thousands of miles around Southern Oregon. And, of course the Oregon Coast is a love of mine so I’ve traversed the shoreline a lot too.

My most recent Oregon road trip didn’t set out to be epic — I was just going to a friend’s birthday campout at the Deschutes River Recreation Area (near The Dalles, OR). But since the timing was perfect — the greenest time of year the beginning of June — one thing led to another and I ended up on a 10-day, 1,500-mile odyssey that covered over half the counties in the State of Oregon (and, of course, the to/from my home in Seattle). Check the map below for my exact itinerary, which is where these photos were taken.

The following photos were safely taken along the road of this trip — on the portion between Bend and The Dalles by way of Joseph — and highlight the diversity of scenery in Oregon.

Bend, Oregon area — Newberry Volcano and Cascade Lakes Scenic Byway

A photo taken looking at Paulina Peak on an Oregon road trip near Bend. There are green fir trees on either side of the road and the snow covered mountain rises up above the road underneath a blue sky.
Paulina Peak, at almost 8,000 feet, is the highest remaining part of the Newberry Volcano.
Ponderosa pine trees rise up from a grassy field along the road, which has a double yellow line.
This Oregon road trip stops amongst the Cascade Mountains which are still snow covered in this photo. There is also snow along side the road.
The Cascade Lakes Scenic Byway opens when the snow melts. In the distance is South Sister and Broken Top.
A black lava flow is visible from the roadside on a drive through the Cascade Lakes Scenic Byway near Bend Oregon. The rusted metal guardrail is slightly visible and there is a large pine tree sharing the blue sky in the photo.
An up close reminder that the Cascade Lakes Scenic Byway weaves through volcanic history, including this “recent” lava flow, which looks like a mound of coal in the distance.

Bend to Burns — lonely highway 20

An up close shot of a highway guardrail covered in stickers that show different places in Oregon.
A lone blue SUV is parked on the side of the road amongst low brush and very dry looking landscape in Eastern Oregon. There is a lone telephone pole amongst the blue sky.
Matthew Kessi takes a selfie while on a road trip around Oregon. He's standing in the middle of the highway and the white lines can be seen on both side. He's wearing a red shirt and squinting a bit from the sunshine.
I looked both ways before standing in the middle of the road. No cars for miles!
Two solid yellow lines flow through this photo leading away down a lonely blacktop highway in Eastern Oregon. The sky is blue and the grassy terrain on either side is flat.
This hillside of pine trees taken from the side of the road on an Oregon road trip shows trees burnt by a recent forest fire mixed in with trees unharmed that are green and thriving.
Ghost forest. Forest fires are an unfortunate reality in the Pacific Northwest. This photo taken in the Blue Mountains (Malheur National Forest) showcases the random power of fire.

John Day to Joseph

Two plates of food are seven on a wood paneled table along with a roll of silverware. One dish is macaroni and cheese covered with tomatoes and chives. The other dish is a Caesar salad with chunks of cheese and croutons.
1188 Brewing Company was a pleasant surprise on the Main Street of Highway 26, which passes through John Day, Oregon. The delicious Mac-n-cheese and tangy Caesar salad provided me with energy to push through the 400-mile day.
The Strawberry Mountains are snow covered in the distance of this photo, which features a pile of large hay bales surrounded by a fence. There is bright green grass in the field behind an old hay trailer.
Near Prairie City, Oregon. The Strawberry Mountains rise up in the background.
A fabricated giant covered wagon sits on the side of a road in Eastern Oregon as an information center for visitors to the region. The wagon wheels are bright red and the wood of the cart is painted green. The canvas top is white.
Oregon Trail wagon train country. This larger-than-life version houses information on sprawling Grant County, Oregon.

Joseph, Oregon — Summer ancestral home of the Nez Perce

The pink hues of sunset begin to swell over the Wallowa Mountains near Joseph Oregon. This photo taken from the side of the road shows a tiny bit of white fencing and a wheel of an irrigation line while the cattle graze out in the distance.
The Wallowa Mountains are sometimes dubbed “The Oregon Alps.”
A white barn with distressed white painting sits in the middle of a field framed in by a metal fence. In the background the Wallowa Mountains rise up toward the blue sky.
This photo taken on an Oregon road trip shows a winding gravel road leading toward the majestic Wallowa Mountains that are still snow capped in the background.
A blue SUV sits at the end of this dirt ranch road behind a gate near Zumwalt Preserve in Northeast Oregon. The sky is peppered with white fluffy clouds and the hill above the vehicle has a fir tree forest.
It’s never advised to trespass in Oregon — but I’m on an official trail that is part of the Zumwalt Prairie Preserve. This trail leading to a viewpoint of Hells Canyon traverses private ranch land.
The back window of a Volvo is covered in mud and dust and the outline of the rear wiper seems to have made a trace through the brown goop. A piece of a Washington license plate can be seen.
A red barn can be seen from the side of the road near Joseph Oregon on a road trip through the Wallowa Mountains, which are snow covered in the background of this photo. The barn has a gray metal roof.
An Oregon History side on the side of the road is worn red painted wood with white letters that briefly describes the Nez Perce people who used to live in this region that is present day Joseph Oregon.
Wallowa Lake is peaceful as a band of forest and meadow show off various textures of green while the snow covered mountains rise toward the blue sky.

Joseph to Dufur — river and wind

A mercantile along the side of the road on a trip through Oregon has a pink sign that says M Crow and the side of the building is painted brown wood.
A hillside lined with giant white windmills reaches up to a blue sky while two orange road signs show arrows pointing in opposite directions. There are pieces of rusted metal leaning up against a barbed wire fence.
A large grain elevator and sheet metal covered barn rise up amongst a dry brownish hill. The road has painted orange lines on blacktop that is smooth.
This shot of the Columbia River flowing through the Columbia River Gorge shows rusted train tacks, an interstate highway with two white cars driving and the mighty river. The hills in the background are brownish colors under a blue sky.

Dufur, Oregon — under the rain shadow of Mt. Hood

This shot taken on an Oregon road trip shows a lonely blacktop road with orange center lines underneath a dramatic system of clouds that look heavy with rain. The fields on either side of the road are fenced in and full of green grass.
This sunset scene taken from the side of a county road in near Dufur, Oregon focuses on a wooden fence post while a hay bale sits in a grassy field. There are several pieces of farm machinery in the background.
The sun is setting behind a farm, complete with a traditional style wood barn and several large metal grain containers. The road in the foreground has a yellow line on the pavement and the clouds above in the blue sky have hints of sunset pinks on them.

Dufur to The Dalles — gorge-ous final chapter

Bright orange poppies with green foliage line the side of a road near the Columbia River in Oregon. The grass is a dry yellow in the field leading to the water. The sky above is blue with scattered clouds.
The curving road near the Rowena Lookout winds up a hill covered with yellow dried grasses and small green trees. The Columbia River is visible in the background. This photo was taken near The Dalles, Oregon.
The historic Columbia River Gorge Highway was built to be dramatic on purpose, and this curvy road lives up to that promise. The Rowena Lookout offers impressive views of the region.
Matthew Kessi smiles for a selfie taken on his Oregon road trip. He's wearing a bright red shirt covered with a black plaid shirt and a black cap on his head. The background is out of focus but shows a green grassy meadow leading toward the Columbia River.
Hiking the McCall Point Trail at the Tom McCall Preserve — wildflowers galore while overlooking the Columbia River Gorge.
The Dalles Bridge leads from Oregon to Washington State and the pinkish metal structure crosses the Columbia River after making a curve.
The Dalles Bridge crosses the mighty Columbia River bound for Washington State.

Interactive Map of my Oregon road trip