The COVID-19 pandemic has left major shifts in transit usage patterns on systems around the world in its aftermath. Unfortunately, the lack of detailed post-pandemic data on passenger travel habits has limited transit agencies’ ability to respond to trends and leverage new travel markets. The rollout of wireless fidelity (Wi-Fi) services at stations and onboard vehicles presents a potential solution, as Wi-Fi device connections can be used to provide very detailed information on customers’ origins, destinations, exact route, and travel time, which in turn can be aggregated by time and geography to reveal broader trends. This study presents an exploratory analysis based on such Wi-Fi data to investigate post-COVID ridership recovery trends on the Toronto subway system, demonstrating that Wi-Fi connections can be a credible proxy for overall ridership. The data show that downtown office commuting has been the slowest-recovering travel market, with local riders in suburban areas, off-peak riders, and discretionary riders returning to the subway system at higher rates. The data also confirm past research findings that less affluent and non-office workers were the fastest to return to transit.