Wireless communications using highly directive terahertz (THz) waves exhibit lower immunity to obstructions than microwaves, limiting their applications. This study demonstrates an obstacle-tolerant THz wireless link established by a self-healing Bessel beam at 300 GHz. The Bessel beam is generated by sending a Gaussian beam through a dielectric axicon lens. Furthermore, experiments were conducted to investigate the short-range transmission (98 mm) reception characteristics with and without the dielectric cubic obstacle (7.5 λ in size) and the metallic obstacle (22 λ in length and 8 λ in width) in the Gaussian beam and self-healing Bessel beam cross sections. The maximum attenuation of the received power due to obstruction was 8.8 and 2.2 dB for the Gaussian and Bessel beams, respectively, when the dielectric obstacle is placed in the middle of the transmission path (49 mm from a transmission lens). This study further investigated the bit error rate (BER) characteristics (1 Gbps, on–off keying) with the dielectric obstacle crossing the beam cross section. When the obstacle crosses the Gaussian beam, the BER degrades as the obstacle approaches the optical axis, breaking the wireless link. In contrast, when the obstacle crosses the Bessel beam cross section, the BER is maintained at <3.8 × 10−3 (the forward error correction limit), and the wireless link is maintained. A self-healing beam, such as the Bessel beam, makes the THz wireless link more tolerant than the Gaussian beam to obstacle and expand applications for THz wireless communications.