Soft tissue-to-bone interfaces, also called entheses, are found throughout the human body, typically linking structures like tendons, ligaments, and the meniscus to bone. These structures are of great interest to both the materials and biomedical engineering communities due to their unique properties and clinical relevance. The enthesis links highly dissimilar materials, often mediating a multiple order of magnitude change in stiffness, over only a few hundred microns. Such a feat has not yet been created in synthetic structures. Clinically, these tissues are often replaced during the repair of the meniscus, ligaments, and tendons. While the enthesis does not often tear, the reconstruction of the enthesis by the body is difficult due to the minimal vascularity and innervation in this region. As such, when adjacent soft tissue structures (ligaments, the meniscus, etc.) are damaged, clinicians will often include the enthesis from a cadaveric replacement tissue to avoid a need for recapitulating this structure. These examples highlight the importance of this tissue and the need to understand the mechanisms by which it functions. This dissertation begins with a review of the soft tissue-to-bone interfaces and previous methods utilized by researchers to engineer these structures. After this discussion, a study analyzing the development of a structure-function relationship for the meniscal enthesis is detailed. This study utilizes Raman imaging and confocal elastography for the spatial correlation of composition, structure, and mechanics, finding new mechanical mechanisms within the soft tissue of the enthesis, as well as an overall picture of the enthesis at the microscale. The techniques developed in this study are then extended to other systems for the development of high resolution, non-destructive imaging of the exact concentration of different biochemical components found in articular cartilage. This technique has the clinical potential for analyzing local cartilage composition on living tissue. Information learned from the analysis of the enthesis is then applied for the development of interfacial scaffolds for tissue engineering the enthesis. These scaffolds possess an interface between mineralized and unmineralized tissue that has application for interfacial engineering. Lastly, a study focusing on the development of a laboratory for introducing engineering to early-stage students is discussed. This laboratory is directed establishing critical thinking skills revolving around engineering and design in up-and-coming scientists. Supplemental information for this dissertation includes Movies 2.1 – 2.12 and Movie 4.1, which can be accessed online.