In this study, a Wi-Fi system with a tethered balloon is proposed for the teleoperation of vehicular forestry machines. This system was developed to establish a Wi-Fi communication for stable teleoperation in a timber harvesting site. This system consisted of a helium balloon, Wi-Fi nodes, a measurement system, a global navigation satellite system (GNSS) antenna, and a wind speed sensor. The measurement system included a GNSS module, an inertial measurement unit (IMU), a data logger, and an altitude sensor. While the helium balloon with the Wi-Fi system was 60 m in the air, the received signal strength indicator (RSSI) was measured by moving a Wi-Fi receiver on the ground. Another GNSS set was also utilized to collect the latitude and longitude data from the Wi-Fi receiver as it traveled. The developed Wi-Fi system with a tethered balloon can create a Wi-Fi zone of up to 1.9 ha within an average wind speed range of 2.2 m/s. It is also capable of performing the teleoperation of vehicular forestry machines with a maximum latency of 185.7 ms.