The load distribution in multi-dowel timber connections under bending moments was investigated by means of an integrative evaluation of a hierarchically organized test program, which encompassed component tests as well as single-dowel and multi-dowel connection tests. It was demonstrated that the anisotropic material behaviour of Laminated Veneer Lumber, and consequently of wood in general, leads to a non-uniform load distribution among the dowels, even for multi-dowel connections with a circular arrangement of dowels. Model predictions from this study highlight inefficiencies of the simplified calculation approach, based on the polar moment of inertia, i.e., based on isotropic theory. Loads of dowels loaded parallel to the grain were found to be underestimated by up to 50%. Through the hierarchically organized experimental campaign with full-field deformation measurement techniques, load distribution effects could be related to the orthotropic material behaviour of wood expressed in terms of load-to-grain angle dependent slip curves of single-dowel connections.