In 1819, Weakley, along with several other notable early Nashville residents such as Dr. John Shelby, petitioned the Tennessee Assembly for permission to establish the Nashville Bridge Company. Weakley and Shelby subsequently served as commissioners for the newly formed company. By 1823, the Nashville Bridge Company's first bridge project, which was also the first covered bridge to span the Cumberland River, was completed near the Public Square in Nashville at a cost of $75,000. This bridge was demolished in 1851 to allow for larger and taller steamboats to access the commercial wharfs at Nashville.