After finding a tiny image of the flying flag (as on Wikipedia https://en.wikipedia.org/wiki/Winsted,_Minnesota#/media/File:2012-0814-WinstedCH-new.jpg), I found larger partial images of the flag. This is the best: http://www.hjblogs.com/wp-content/uploads/award.2.jpg

Using a downloaded city logo, I made the attached image as my best guess.
Masao Okazaki 11 August 2019