This achievement takes up the majority of the game but don't fret its ridiculously easy.
1.Collect the items the giant arrow guides you to
2.After the cheerleader distraction at University University goto the petting zoo and grab the window that doesn't look like a window in the ostrich area.
3.You get a wagon wheel near the upper right of the middle section of the fair
4.Theres a weather vane back home after your date with your dreamboat oh boy