Dr. Kenneth E. Bailey spent 40 years of his life living in the Middle-East (as a missionary). Along with earning multiple advanced degrees in theology Bailey has written exstensively on the issue of Middle-Eastern culture, providing a fanstic contribution to understanding the cultural of the Gospels. 

This book specifically will provide a background for understanding many of the details that is lost on our current American culture.  

A larger work (by Bailey) that gives a larger overview of Middle-Eastern culture in the Gospels. This book is a great resource for any study of the Gospels

This work has become a standard fixture for Biblical Scholars (but is fairly accessable for the layman as well). Here, Joachim Jeremias recreates the 1st century culture and background of Jerusalem/Palestine.