The cultural heritage of fortresses is often exposed to external elements, leading to significant damage from stone weathering and natural disasters. However, due to the nature of cultural heritage, dismantling and restoration are often impractical. Therefore, the stability of fortress cultural heritage was evaluated through non-destructive testing. The durability of masonry cultural heritages is greatly influenced by the physical characteristics of the back-fille material. Dynamic characteristics were assessed, and endoscopy was used to inspect internal fillings. Additionally, a finite element analysis model was developed considering the surrounding ground through elastic wave exploration. The analysis showed that the loss of internal fillings in the target cultural heritage site could lead to further deformation in the future, emphasizing the need for careful observation.