The Bridge Over Maitland Run · 1890 Leaning on the rail of a bridge over Maitland Run, this boy may have stopped to rest on a hot summer day. Perhaps he was thinking about fishing . . . or jumping into the cool water of the canal that connects Lake Maitland and Lake Osceola! A much newer bridge on Palmer Avenue extends over a canal that is bordered by many homes and lush gardens. The canal carries a good deal of boat traffic between Winter Park’s “chain of lakes.”