The human forefoot presents an interesting biomechanical problem of clinical importance because loads are distributed unequally across multiple bones. The fact that long bones typically have a several-fold safety factor relative to peak loads suggests that metatarsal strengths should be related to their peak loads. This study is the first to systematically examine the cross-sectional geometric properties of the human forefoot and their relationship to external loads during walking and running. We report midlength cross-sectional geometric properties (CA, Ix, Iy, Imax, Imin, J, Zx, and Zy) of metatarsals (1–5) and the hallucial proximal phalanx of a shod industrial population (n = 40) obtained using computed tomography. We then examine the relationship between these measures of shaft strength and published plantar pressure data sets recorded during the following functional activities: standing, at the push-off stage of the walking cycle, the full walking cycle, and running. Cross-sectional geometric properties of the first ray are greater than those of other rays, even when scaled to bone length. This pattern corresponds to the high pressures recorded for the first ray during most activities. The relationships between cross-sectional geometric properties of the lateral metatarsals and peak plantar pressure data are more complex. Metatarsals 2–4 are weakest in most cross-sectional geometric properties. However, metatarsal 2, and to a lesser extent metatarsal 3, experience relatively high peak pressures. On average, geometric measures of axial and bending strengths (adjusted relative to body size) are lower in females than males, and in European Americans than in African Americans, which corresponds to the respective rates of general metatarsal stress fracture in these groups. The discrepancy between strength and plantar pressure values in metatarsals 2 and 3 is consistent with the high incidence of stress fractures in these bones and underscores the importance of soft tissues, such as the plantar fascia and flexor musculature, in moderating metatarsal shaft strain.