Fugitives - The Farmstead
Upon reaching the farm, choose either option to get rid of the old people. Now, go to the front yard and climb the windmill nearest the barn. As Leo, interact with the windmill multiple times to cause it to spin and unlock the achievement for both players.
This achievement can be seen in the video guide at 3:48:NOTE:
Achievements are only available to owners of the game. Players using the "Free Trial" friend pass will NOT unlock achievements.