The foot is a highly complex biomechanical system for which finite element (FE) modeling has been used to evaluate its loading environment. However, there is limited knowledge of first metatarsophalangeal (MTP) and first metatarsocuneiform (MTC) joint contact mechanics. Our goal was to develop a framework for FE modeling of the medial forefoot which could accurately predict experimental measurements of first MTP and first MTC joint loading. Simulations of planus and rectus foot types were conducted for midstance of gait. A custom-built force-controlled cadaveric test-rig was used to derive intracapsular pressure sensor measurements of contact pressure, force, and area during quasi-static loading. The FE model was driven under the same boundary and loading conditions as the cadaver. Mesh sensitivity analyses and best-fit calibrations of moduli for first MTP and first MTC joint cartilage were performed. Consistent with previous experimental research, a lower compressive modulus was best-fit to the first MTP compared to first MTC joint at 10 MPa and 20 MPa, respectively. Mean errors in contact pressures, forces, and areas were 24%, 4%, and 40% at the first MTP joint and 23%, 12%, and 19% at the first MTC joint, respectively. The present developmental framework may provide a basis for future modeling of first MTP and first MTC joint contact mechanics. This study acts as a precursor to validation of realistic physiological loading across gait to investigate joint loading, foot type biomechanics, and surgical interventions of the medial forefoot.