The deployment of dedicated short-range communications (DSRC) roadside units (RSUs) allows a connected or automated vehicle to acquire information from the surrounding environment, such as a traffic light’s signal phase and timing, using vehicle-to-infrastructure communication. Several scholarly papers exist on planning strategies for DSRC RSU deployments using simulation without accounting for wireless communication constraints and environmental changes. This paper proposes an empirical-based planning strategy for a highway off-ramp in a real-world environment. The research goal focuses on developing a low-cost and structured deployment plan for DSRC RSUs with the following objectives: use free planning tools; apply the deployment strategy in a real-world environment; utilize publicly available DSRC RSU data measurements; and leverage existing intelligent transportation systems infrastructure when possible. The proposed planning strategy includes three steps: (1) conduct a virtual site survey, (2) gather baseline performance data for the DSRC RSU equipment, and (3) generate a predictive radio frequency signal. The planning strategy was successfully applied on a highway off-ramp at exit 19A of the Capital Beltway, which encircles Washington, DC.