This chapter presents data based on travel epistles about how the Byzantines perceived forest lands, a feature of the environment that dominates the mountain landscape. The forest becomes an integral part of the travel epistles when the scholars cross dense wild areas in the mountains. The travel epistles pertaining to “Woodlands” also provide valuable information about the state of forests during the Late Byzantine period, as well as cultural contexts and perspectives of these highland areas, mainly in Thrace, Macedonia, and northwest Asia Minor and span from the late twelfth to mid-fourteenth century. The scholars travel to frontier territories of the empire during periods of unrest, which adds to the adventurous nature of these journeys. The overall presentation of these two groups defines distinct similarities yet also clear differences in the perceptions of forest areas. Most descriptions on deserted areas and highland forests are emotionally charged due to the unpredictable human agency rather than any other supernatural or symbolic associations found in other texts.