Stratford was named by Canada Company director Thomas Mercer Jones, and William Sargint. (see Sargint Street).  Apparently, or so the story goes, Jones also had a hand in naming the Shakespeare Hotel. Sargint supposedly received a sign from Jones to advertise the inn. It was a picture of Shakespeare; the rest is history. 

From the beginning, cultural connections with Stratford (Ontario) and Shakespeare were in evidence. In 1859, Stratford was divided into five wards each reflecting the Shakespearean connection: Avon, Falstaff, Hamlet, Romeo and Shakespeare. Some street were drawn from Shakespeare's works, and early on there were cultural activities and theatrical undertakings.

In April 1864, the Shakespeare tercentenary (his 300th birthday) in Stratford was well attended despite a day of rain. Umbrellas are visible in a picture of those gathered in Market Square, but not all were deterred. Even then, Stratford loved a good party.

It was a gala occasion. The British connection was strong. A “Centennial Oak” (see Erie Street) was planted in Shakespeare’s honour next to the location of the Shakespeare Hotel, which had burned in 1849.
Activities after the tree-planting ceremony included a fancy commemorative ball, on April 26, the date of Shakespeare’s baptism. The ball, in the town hall, began at 9 p.m. Tickets were $2 per person.       Source: Gord Conroy