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All achievements can be obtained in one playthrough. I have tried to arrange the achievements in chronological order.
Road 96 Achievements Guide
Collect’em All
Cassettes can be found on the level, someone from the NPC can give them to you and you can still buy them ($ 10). There are 18 audio cassettes in the game. If you missed them, then in the New Game + they will remain with you. You can get from 1 to 2 cassettes on one level. In general, all of them can be obtained in one playthrough of the game.
Cat Person
In the first episode, there will definitely be a mission where you will meet Zoe at the campsite. I need to pet the cat. Screenshot to help.
Road Pals
You will meet Zoe for the first time, where the cat was stroked (camping). This is a story achievement you won’t miss.
A Light in the Darkness
In the first episode, where you first meet Zoe at the campsite. It is necessary when you are sitting by the fire and Zoe begins to warm her hands, the inscription “blow on fire” will appear near the fire. Do this and get the achievement.
Homesick
When you see a phone booth, select the option to call home. It costs $ 1.
Campaign Funder
We need to donate money for the election campaign. At the phone booth, select the “use” option ($ 1). Dial 96555 (Tirac) or 96777 (Florres). And then you can donate money ($ 10). In total, you should have $ 11 in your pocket.
Help a Friend
When there is a mission where Zoe is handcuffed to a police car, just help her escape. This is a story achievement you won’t miss, but you can get caught and then you can do it only in the second playthrough.
Almost There
You need to get to Route 96 for the first time. This is not very difficult to do, considering that for the full game you will need to get there many more times.
Hard Choice
In one of the episodes, you will cross the border with Zoe. At the very end, you will have the choice to save her or leave on your own. Choose any of these options and you will receive the achievement. It is impossible to miss it.
Stone After Stone
When you get to Route 96, there will be a waterfall and a cave nearby. There is a mountain of stones in the cave. You need to add one stone each time you get there and so on 3 times.
Old Pro
You need to get 6 times to Route 96. You can go to jail and die when crossing the border, as Route 96 is counted when you get to the location with a waterfall and a cave.
Border Master
You just need to complete the entire game and you will receive this achievement.