The town lies off the N11 route between Dublin and Wexford. Wicklow is also connected to the rail network with Dublin commuter services now extending to the town. Additional services connect with Arklow, Wexford and Rosslare Europort, a main ferry port. There is also a commercial port, mainly importing timber.
The origin of the Irish name Cill Mhantáin has an interesting folklore of its own. Saint Patrick is said to have attempted to land on Travailahawk beach, to the south of the harbour. Hostile locals attacked the landing party causing one of the saint's party to lose his front teeth. Manntach (toothless one), as he became known, was undeterred and returned to the town, eventually founding a church. Hence Cill Mhantáin, meaning Church of the Toothless One, although there is no evidence, material or written, for the existence of such a local holy man.
The English-language 'Wicklow' placename bears no relation to the Irish Cill Mhantáin. The Normans, who came to dominate the area, preferred the non-Gaelic placename. The Norman influence can still be seen today in some of the town's place and family names.
After the Norman invasion, Wicklow was granted to Maurice FitzGerald who set about building the 'Black Castle', a land-facing fortification that lies ruined on the coast immediately south of the harbour.
The surrounding County of Wicklow is rich in bronze age monuments. The oldest surviving settlement in the town is the Franciscan Abbey, located at the west end of Main Street, within the gardens of the local Roman Catholic parish grounds.
Other notable buildings include the Town Hall and the Gaol, built in 1702 and recently renovated as a heritage centre and tourist attraction. The East Breakwater, arguably the most important building in the town, was built in the early 1880s by Wicklow Harbour Commissioners. The architect was William George Strype and the builder was John Jackson of Westminster. The North Groyne was completed by about 1909 - John Pansing was the designer and Louis Nott of Bristol the builder. The Gaol was a place of execution up to the end of the 19th century and it was here that Billy Byrne, a leader of the 1798 rebellion, met his end in 1799. He is commemorated by a statue in the town square. The gaol closed in 1924 and is today a tourist attraction with living displays and exhibits.
At Fitzwilliam Square in the centre of Wicklow town is an obelisk commemorating the career of Captain Robert Halpin, commander of the telegraph cable ship Great Eastern, who was born in Wicklow in 1836.