Poly(glycerol sebacate) (PGS) is an elastomeric polymer which is attracting increasing interest for biomedical applications, including cartilage regeneration. However, its limited mechanical properties and possible negative effects of its degradation byproducts restrict PGS for in vivo application. In this study, a novel PGS–bioactive glass fiber (F18)-reinforced composite was developed and characterized. PGS-based reinforced scaffolds were fabricated via salt leaching and characterized regarding their mechanical properties, degradation, and bioactivity in contact with simulated body fluid. Results indicated that the incorporation of silicate-based bioactive glass fibers could double the composite tensile strength, tailor the polymer degradability, and improve the scaffold bioactivity.