Daddy Long Legs by Jean Webster

Jerusha Abbott has spent her whole life in the John Green Asylum for Orphans . . . until an anonymous trustee decides to send her to college.  His only stipulation?  That she must write a letter each month detailing her education and its progress.  So Jerusha heads off to college and the experiences of a lifetime.

This is a wonderful book for anyone who liked Little Women or the Anne of Green Gables series.  The entire story other than the first chapter set in the orphanage is told through Judy's letters to her benefactor whom she calls Daddy Long Legs.  The audio version of the book is also great with a narrator that invests a lot of emotion into the reading.