Active chitosan-based films, blended with fibrous chestnut (Castanea sativa Mill.) tannin-rich extract were used to pack Gouda cheese that has been contaminated with spoilage microflora Pseudomonas fluorescens, Escherichia coli, and fungi Penicillium commune. A comprehensive experimental plan including active chitosan-based films with (i) chestnut extract (CE), (ii) tannic acid (TA), and (iii) without additives was applied to evaluate the film′s effect on induced microbiological spoilage reduction and chemical indices of commercial Gouda cheese during 37 days while stored at 4 °C and 25 °C, respectively. The cheese underwent microbiology analysis and chemical assessments of ultra-high-performance liquid chromatography (UHPLC) (cyclopiazonic acid), pH, and moisture content. The biopackaging used for packing cheese was characterized by mechanical properties before food packaging and analyzed with the same chemical analysis. The cheese microbiology showed that the bacterial counts were most efficiently decreased by the film without additives. However, active films with CE and TA were more effective as they did not break down around the cheese and showed protective properties against mycotoxin, moisture loss, and pH changes. Films themselves, when next to high-fat content food, changed their pH to less acidic, acted as absorbers, and degraded without plant-derived additives.