This paper focuses on the little-known but important cave-sanctuary of Zar Trypa on Mount Ossa (modern Kissavos) in north-eastern Thessaly. In 1910, research conducted at the site uncovered remains of votives from the Classical, Hellenistic and Roman periods, including a group of eight inscriptions dedicated to the Nymphs. Despite this remarkable epigraphic assemblage, the site was not investigated beyond a single excavation season and today is largely unknown. Consequently, the Zar Trypa cave and its finds have never featured prominently in the discussion of Thessalian religion or of Greek ‘natural’ sanctuaries. Combining archival studies, on-site observations and GIS-based methods of landscape archaeology, this paper sets out to re-assess the surviving archaeological evidence from the Zar Trypa cave, to examine the spatial setting of ritual activity at the site, and to place the cave in the context of Mount Ossa's natural environment and ancient settlement pattern. Drawing on the methodological framework of ‘lived religion’, this assessment not only contributes towards our understanding of ancient religious experiences at the Zar Trypa cave, but also addresses broader questions such as the significance and meaning of ‘sacred travel’ in pre-Christian antiquity.