This is the flag of the town I grew up in.
"The flag consist of the word “Tillsonburg” in blue lettering in between twigs of Maple Leaf branches; an Otter, Tillsonburg’s symbol, with Edwin Delevan (E.D.) Tillson’s motto “Forward” underneath it with the date 1872 signifying when Tillsonburg was incorporated from a village into a Town. That date also marked when E.D. Tillson was elected as Tillsonburg’s first Mayor. George Tillson, E.D. Tillson’s father, settled the area in 1825 who is known as the founder father of Tillsonburg."
The giant T is what kills it. Otherwise it's a pretty decent design, I think. Maybe I'll take a crack and redoing it sometime.