Six college students discover their dorm was once an insane asylum that conducted gruesome lobotomies on its teenage inmates during the 1930's.

In this new comedy adventure, celebrated travel writer, Bill Bryson (Robert Redford), instead of retiring to enjoy his loving and beautiful wife, Catherine (Dame Emma Thompson), and large and happy family, challenges himself to hike the Appalachian Trail - two thousand two hundred miles of America's most unspoiled, spectacular and rugged countryside from Georgia to Maine. The peace and tranquility he hopes to find, though, is anything but, once he agrees to being accompanied by the only person he can find willing to join him on the trek - his long-lost and former friend Stephen Katz (Nick Nolte), a down-on-his-luck serial philanderer who, after a lifetime of relying on his charm and wits to keep one step ahead of the law - sees the trip as a way to sneak out of paying some debts and sneak into one last adventure before its too late. The trouble is, the two have a completely different definition of the word, "adventure". Now they're about to find out that when you push yourself to the edge, the real fun begins.

Ben Baker is a man-child who lives on his friend's couch getting high. His friend, Steve Dallas, is a moderately successful weather reporter who is living a superficial life. When Ben receives word that his father has died, Steve drives him home and they re-connect with Ben's successful and driven sister Terri and hippie step-mother Angela who is the same age as they are. The reading of the will drives Ben to come up with a new purpose in life, but those around him don't prove to be very supportive, and then they all re-examine their own life.