@dillyd It depends what type of trip you want it to be, there is so much out here. Some of my favorites:

Hiking among the Cascade Range volcanoes (Jefferson, Hood, Bachelor, Three Finger Jack, Three Sisters).

Timberline Lodge near Mt. Hood.

Multnomah Falls

Crater Lake National Park (before our government makes it implode).

Cape Kiwanda and Pacific City on the coast.

Charleston and the string of state parks (Shore Acres, Sunset Beach) near Cape Arago.

Steens Mountain and the Alvord Desert and hot springs in the southeast

Newberry Volcanic Monument in central Oregon.

Owyhee Canyonlands.

Astoria and the North Coast.

Neahkanie Mountain and Cape Falcon trails.

Cape Lookout State Park.

John Day Fossil Beds.

Oregon's Painted Hills.

Pendleton Round Up (big rodeo).