Wood is poised to become a material of choice for future construction. When appropriately managed, it is a renewable material with unique mechanical properties. Thus, there has been a growing demand for hardwoods, including Castanea sativa Mill., the focal point of this investigation, for structural applications. Albeit in a limited capacity, Eurocode 5-2 offers friction coefficients for softwoods, but it falls short for hardwoods. These coefficients play a critical role in numerical simulations involving friction, enabling the optimization of joints and, by extension, the overall structural integrity. Test samples were evaluated at 15% and 18% moisture content (Service Class 2) for various orientations of timber-to-timber and timber-to-steel friction. The results provide an experimental database for numerical simulations and highlight the influence of moisture on the stick–slip phenomenon, which was absent for the timber-to-timber tests, as well as on the rising friction values. At 18%, the static and kinetic coefficients were 0.70 and 0.48 for timber-to-timber and 0.5 and 0.50 for timber-to-steel. The increase was around 50% for timber-to-timber friction and over 170% for timber-to-steel pairs. Moreover, the findings proved a relationship between both coefficients and the validity of the linear estimation approach within the 12–18% moisture commonly applied to softwoods.