This thesis addresses Constantine's developments of the Roman province of Palaestina. It analyzes two important Christian bishops, Eusebius of Caesarea and Cyril of Jerusalem, and one nameless Christian traveler, the Bordeaux pilgrim, to illuminate how fourth-century Christians understood these developments. This study examines the surviving writings of these Christian authors: the Bordeaux Itinerary, Cyril's Catechetical Lectures, and Eusebius's Ecclesiastical History, Onomasticon, Preparation of the Gospel, Proof of the Gospel, and the Life of Constantine, and the archaeological remains of several Constantinian basilicas to interpret their views of the imperial attentions that were being poured into the land. Together these accounts provide views of fourth-century Palaestina and Jerusalem that when combined more fully illuminate how Christians understood Constantine's Holy Land policy. This study focuses on Constantine's developments of the city of Jerusalem, primarily the so-called Triad of Churches (The church of the Nativity, the Eleona, and the Holy Sepulchre) built in and around the city. It likewise considers the countryside of Palaestina outside of Jerusalem. While some Christians were resistant to the developments of Jerusalem, our sources reveal how many Christians supported, or at least desired to experience, the newly developing Christian Holy Land. This thesis argues that most of the discrepancies over the city of Jerusalem between our sources, especially Eusebius and Cyril, developed from long-standing political tensions between the cities of Caesarea and Jerusalem. The Bordeaux pilgrim, on the other hand, traveled across the Roman Empire to see and experience the developing sites throughout the land with no interest in local political debates. With this added perspective we can see how Christians, separated from the positions of church fathers, experienced the developing Holy Land.