Alternative bracing systems have been widely applied in heavy timber structures due to its contribution to lateral stiffness and strength, while the improvement in the ductility and energy dissipation capability is limited. Friction damped knee brace is applied in this paper to reinforce rotational behavior of the bolted post-to-beam glulam connections. Monotonic and cyclic loading experiments were conducted on fifteen full-scale specimens. The failure modes, elastic stiffness, moment capacity, hysteresis response and energy dissipation were evaluated and analyzed. The experimental results indicated that with the installation of friction damped knee brace, extremely large initial stiffness was achieved and the moment capacity and accumulated energy dissipation of the post-to-beam connections were increased by 207% and 950%, respectively. Moreover, a multi-segment theoretical model was proposed to predict the rotational behavior of the reinforced bolted glulam connections. The theoretically predicted moment-rotation curves showed good agreement with the experimental results.