For this achievement, you need to find 3 chessboards and interact with them. All 3 are located in different houses/cabins.
1) inside the Roy's house
2) inside cabin A north of the store
3) inside the "northern" cabin (the one with the crossbow bolt sticking out the right side. Key for this cabin is in a shack located in between cabin A and B)
Hopefully this guide has helped you!