The Beaver State "Discover every city in Oregon"
You just have to visit every city (14) in Oregon. Make sure to see the "city discovered" message pop up.
Uplifting "Travel across the New Youngs Bay Bridge"
The bridge can be found on Route 101 right before the Astoria text on the map.
Travel Oregon "Discover following landmarks of Oregon: Crater Lake, Crooked River Gorge, Thor's Well and Yaquina Head Lighthouse"
Yaquina Head Lighthouse Can be found on Route 101 between Coos Bay and Newport.
Crater Lake Can also be found while travelling the Route 101, this time right after Newport, to the north of the city. You have to drive off the Route 101 onto a small road to get to it.
Crooked River Gorge To get to this landmark you have to take Route 97 from Bend to Klamath Falls and drive off into a street leading to a toll gate.
Can also be found by traveling the Route 97 but this time north of Bend on the way to The Dalles.
Cabbage to Cabbage "Complete a delivery of vegetables over Cabbage Hill"
This achievement can be unlocked while driving on the Route 84 at a specific spot between Pendleton and Ontario. However, as already said in the achievement description you need to deliver vegetables while taking this route to get it unlocked. Now there are vegetables and frozen vegetables in the game.
The achievement unlocks once you enter the passage from either direction on the following screenshot, so you don't have to finish the delivery (contrary to what the achievement description says).
Lumberjack "Deliver cargo from all timber harvest sites in Oregon"
This achievement requires you to transport a commodity from each of the 5 timber harvest sites in Oregon. On the map, the harvest sites are always marked by what appears to be a half of a sawblade as symbol. Since there are more than 5 areas with this symbol in Oregon you have to look at what the area looks like. If there are no buildings (black squares) marked inside the area, it is a harvest site.
Here are the locations of all the harvest sites:
The first one can be found to the east of Newport
The second one can be found in Astoria
The third one can be found to the east of Salem
The fourth one can be found to the south-west of Medford
The fifth one can be found to the south of Bend
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