You made it to Stratford! Nice selection, though you left out the Festival Theatre and the old Ontario Normal School building beside it, both must-sees. I've blathered about the pros and cons of living in Stratford on this and that other forum, so no need to say anything further. It's definitely the Canadian champ for quaintness in the 30,000 to 50,000 population category, no question. (EDIT: Pardon my ignorance, Charlottetown and Stratford are probably neck and neck).
There has been talk of turning the wide expanse of parking behind city hall in this photo into an urban square or plaza. They even held a design competition a while ago. I hope they actually get around to it, though it's currently used as a bus terminal of sorts and the business owners along these streets are against it due to the inevitable loss of parking. By the way, the two floors above Citi Financial are Loreena McKennitt's (blech) offices.
A few more steps and you would have made it to my house. I live just down from this house in a two-block area littered with B&Bs.