A document of 1385 refers to Bridgegate in the town, which implies that a previous bridge existed on the same site. The road it carries was originally the main route from London and Mansfield to Barnsley, Halifax and Richmond. The current bridge was erected by 1483, when the Chapel of Our Lady of Rotherham Bridge was added. It is of ashlar sandstone and is built on three piers, each with a cutwater.
John Leland, writing around 1540, described a "fair Stone Bridge of iiii arches" and "a Chapel of Stone well wrought". The chapel was dissolved in 1547 and converted into first an almshouse, then the town gaol and finally a shop. The bridge was altered in 1768–69 by John Platt, working for John Carr of York, but was restored to its original dimensions by Reginald Blomfield in 1927, when Chantry Bridge was built alongside. The chapel was restored at the same time.