In medieval documents, Via dell’Olmo is referred to as “Schiaccia Vecchia”. In fact, the word "schiaccia” (crush) indicates the use of stone paving slabs, highlighting Via dell’Olmo’s importance compared to other streets in Santa Fiora, which were simply called “contrade” (districts) and probably not paved. There is a decorated lintel from the 15th century and, on a medieval house, there are two signs engraved by master stonemasons of probable French origin.