Oregon Itinerary

eleven days . six parks . two states


2021 Oregon Road Trip Itinerary

Friday, September 10 to Monday, September 20, 2021

09.10.21 . Day 1 – Fly to Portland.

09.11.21 . Day 2 – Drive to Bend via Mount Hood National Forest. Hike Smith Rock State Park.

09.12.21 . Day 3 – Explore Bend and drive Cascade Lakes Scenic Highway.

09.13.21 . Day 4 – Day one in Crater Lake National Park. Add on Toketee Falls.

09.14.21 . Day 5 – Day two in Crater Lake National Park.

09.15.21 . Day 6 – Drive to Jedediah Smith Redwood State Park and explore.

09.16.21 . Day 7 – Hike in Prairie Creek Redwood State Park.

09.17.21 . Day 8 – Meander up the Oregon Coast, end in state capital city; Salem.

09.18.21 . Day 9 – Visit Silver Falls State Park then jet over to Cannon Beach and Haystack Rock.

09.19.21 . Day 10 – Explore Ecola State Park and then return to Portland.

09.20.21 . Day 11 – Fly home.


When and with whom

Scott and I were celebrating the milestone of 10 years of traveling together the best way we knew how, with an adventure. Oregon was a great place to embark on this milestone adventure together, it was an outdoor focussed trip containing many memorable hikes and amazing views. From the classic coast, to the tower redwoods, and so many waterfalls, this Oregon itinerary did not disappoint.

We decided to wait until after Labor Day to take this trip as it marks the end of the busy summer travel months but the weather is still plenty warm for an enjoyable outdoor trip. Excepting some rain, we experienced great weather and zero crowds.


Silver Falls State Park
Oregon Trees
Jeep in Redwoods
Scenic Byway Oregon Itinerary
Smith Rock Oregon Itinerary

Oregon Coast Itinerary
Crater Lake National Park Oregon
Cannon Beach Oregon Coast