Pick The Hill map and the D-535. Equip it with the garage parts, the garage trailer (4 garage points) and head straight from 1 to 2. There is a pretty scary descent down the hill but believe me, this is actually the hardest part. And if you fail you can quickly start over. After unlocking the second garage head to 3 for the great C-255. Equip it with a crane and a medium log cart and go to the log kiosk (4). My recommended route is visible on the screenshot, just
be carefully near the lake - stay close to the shore. Go straight to the objective (5) and don't forget to fuel up at the second garage. Do it two times and cheevo is yours.
You will also get
and if you choose the hardcore difficulty
The HILL achievement in SPINTIRES worth 30 pointsFinish the Hill level in Hardcore mode