Terraced landscapes are characterized by many features but are also threatened by abandonment, with the loss of the historical landscape and increased hydrogeological risk. In this research, we developed an innovative integrated approach using expert-based assessment and evaluation of winegrowers’ perceptions to investigate the coevolution between terraced landscapes and rural communities. The aims were as follows: (i) to identify the historical landscape elements, (ii) to identify the landscape dynamics, and (iii) to analyze winegrowers’ perceptions about the historical landscape elements and future development prospects. The methodology was applied to a terraced vineyard landscape (545 ha) located in Piedmont (Italy). The expert-based assessment included historical analyses and field surveys. To evaluate winegrowers’ perceptions, an online questionnaire was used to understand their perceptions about the landscape’s historical elements and dynamics. The results suggest that unique historical landscape elements and traditional practices (vine pergolas supported by stone columns) are conserved in the area, but also highlight some dynamics, including new vine-breeding techniques (espaliers) and new land uses (olive groves, meadows, and woodland). Winegrowers (n = 49) recognized as identity elements the same identified as historical by experts. Regarding future prospects, almost all winegrowers preferred the conservation of vineyards and pergolas. The research methodology was able to show the mutual link between terraced landscapes and rural communities in coevolutionary terms and could be replicated in similar contexts. According to the winegrowers’ awareness, future planning strategies will have to support dynamic conservation of the landscape.