Aside from the THEATRE type attractions and nice stuff stemming from that, I did find that Stratford's geography also helps in making it an appealing place. The flood control lake aside, downtown appears to be on the confluence of 3 (2.5?) different land surveys askew at different angles, which has resulted in both the city hall/square setup and a downtown that encompasses multiple blocks in different directions and neigbhourhoods stretching off in radials. Most smaller Ontario cities have very... linear downtowns, which is fine, but can make for a less interesting places. Some of the other more interesting places also share unique layouts.
Stratford:
https://goo.gl/maps/EWnyvp9WhqDGRERh9
Slightly larger Woodstock:
https://goo.gl/maps/Fb99M8fFwqk39dmu5