The tendon to bone insertion site is a complex transitional region that links two very different materials. The insertion site must transfer a complex loading environment effectively to prevent injury and provide proper joint function. In order to accomplish this load transfer effectively, the properties of the insertion site were hypothesized to vary along its length. The quasilinear viscoelastic (QLV) Model was used to determine biomechanical properties, polarized light analysis was used to quantitate collagen orientation (structure), and in situ hybridization was used to determine the expression of extracellular matrix genes (composition). All assays were performed at two insertion site locations:​ the tendon end of the insertion and the bony end of the insertion. Biomechanically, the apparent properties of peak strain, the coefficients (A and B) that describe the elastic component of the QLV model, and one of the coefficients (τ1) of the viscous component of the model were significantly higher, while another of the coefficients (C) of the viscous component was significantly lower at the tendon insertion compared to the bony insertion. The collagen was significantly more oriented at the tendon insertion compared to the bony insertion. Finally, collagen types II, IX, and X, and aggrecan were localized only to the bony insertion, while decorin and biglycan were localized only to the tendon insertion. Thus, the tendon to bony insertion site varies dramatically along its length in terms of its viscoelastic properties, collagen structure, and extracellular matrix composition.