Spiders have always fascinated humankind as whilst they are often reviled, their product, the web and its silk, are commonly viewed in awe. As such, silks’ material properties and the fear and fascination surrounding the animals that spin it are seen to play an important role in the development of many cultures and societies. More recently this is even more so with the formalization of this inspiration in scientific and technical communities through biomimetics. The aim of this work is to reflect on the beginnings of our relationship with silk and discuss concepts associated with spider silks and webs in ancient Greek and Roman times whilst comparing this with our current understanding of the field. In this way, ancient texts, namely Greek and Latin ones, are found to intersect with modern advanced disciplines, ranging from architecture to medicine to physics. This allows us not only to understand how natural observation has evolved from antiquity to today, but also how such a highly interdisciplinary research network has been spun by some shared conceptual threads.