Crossing the Clashawley River at the end of Main Street, the structure known as Madam's Bridge takes its name from the gate that once stood immediately to its east, Madam's Gate, which controlled the western entry into this medieval Tipperary town. The gate is long gone, pulled down around 1880, but its commemorative plaque was rescued and set into the bridge's left-hand wall, where it remains.

The bridge itself, built of roughly coursed limestone rubble with three round arches and a parapet, is older than it might first appear, and looking at it closely reveals two distinct phases of construction. The southern, downstream face is the earlier portion; its arches are formed with narrower voussoirs, the wedge-shaped stones that lock an arch together, set on edge in a manner typical of pre-1700 work. The Grace map of 1708 shows the bridge already in place, though its close connection with the medieval gate suggests there was a crossing at this spot even earlier. A plaque once on Madam's Gate credited a John Delahunty with building the bridge, but the more likely reading is that he oversaw a substantial repair in 1742, with medieval fabric surviving beneath the later work. The northern, upstream face tells a different story: wider, rusticated voussoirs characteristic of nineteenth-century construction, along with cutwaters, the projecting piers that deflect river current away from the arch foundations. Ordnance Survey mapping shows the bridge in a narrower form in 1840, and by 1845, on the Grove map, it appears at its current width, confirming that the expansion happened within that short window.