Sri Lanka inherits a rich vibrant history of traditional arts. History of Sri Lanka is divided in to two different categories, pre historic and historic. In historic .era Illustrations, Literature used to depict the Buddhist tradition in aesthetic manner. Past or the heritage will depicts what is the path that we traveled from exist. Paintings of Kandyan period especially the religious paintings could be described as this climax of traditional Sri Lankan paintings. It reflects the both the religious influence together with the Landscape in the broad content. The art craft and architecture were to Sri Lanka with the advent of Buddhism in 3rd Century B.C. In a many ways Sri Lankan art is an expression of it long and enduring Buddhist tradition that has absorbed and internalized numerous regional and local tradition for thousands of years and inspired and influenced by both surrounding Landscape and socio cultural settings. Traditional historiography presents Sri Lankan arts and paintings throughout the pre-modern Sri Lanka and it appeared as religious and non religious influences largely by the Nature. Dynamic, complexion and expressive narration of the classical tradition was transformed and Sri Lankan paintings were come to its climax during the Kandyan period. At that time line and colour were used to produce volume of solidity of figurative forms and natural objects in the classical style underwent a transformed in the Kandyan period. The study has looked in to two case studies of Kandyan period namely Oambulla cave temple and Oanagiriga/a cave temple paintings. The surrounding Landscape and its responsiveness to the experience of the Oambulla and Oanagiriga/a cave paintings were studied. An Anotatta Landscape (Oambulla cave3) painting was highly imaginative painting but really the inspiration of the surrounding Landscape and their experiences. It reflected the level of people, religious leaders, Kings and painters philosophical imagination and level of literacy, knowledge and competence appeared by this plate. In Oambulla cave paintings which can be seen variety of natural Landscape principles and elements such as Waterscape, Aquatic plants, Forms and Space creation etc, and were illustrated more things to the viewer. Among the Kandyan period temples, Oanagiriga/a cave temple is identical with its indigenous design of surrounding Landscape and Landscape depiction by the paintings. It largely inspired by the nearby natural Landscape. It is evident that the Sri Lankan paintings were highly inspired and influenced by the religion and cultural settings at that time. Kandyan period paintings were of its climax and associated with the changes nature and life styles.