Timber structures have been widely used due to their low-cost and environmental-friendly properties. It is essential to monitor connection damage to ensure the stability and safety of entire timber structures since timber connection damage may induce catastrophic incidents if not detected in a timely manner. However, the current investigations on timber connections focus on mechanical properties and failure modes, and the damage detection of timber connection receives rare attention. Therefore, in this paper, we investigate the damage detection of four common timber connections (i.e., the screw connection, the bolt connection, the decussation connection, and the tooth plate connection) by using the active sensing method. The active sensing method was implemented by using a pair of lead zirconate titanate (PZT) transducers: one PZT patch is used as an actuator to generate stress waves, and the other works as a sensor to detect stress waves after propagating across the timber connection. Based on the wavelet packet energy analysis, the signal energy levels of received stress waves under different damage extent are quantified. Finally, by comparing the signal energy between the intact status and the damage status of the timber connection, we find that the energy attenuates with increasing severity of the connection damage. The experimental results demonstrate that the active sensing method can realize real-time monitoring of timber connection damage, which can guide further investigations.