Old Photos with unidentified dates or locations

[Charlie B]

Lets let the title say it but post as much information as you can     

This one was taken in Wooster, Ohio. look at it and pick out clues as to the time frame and the area. It is fun to study a picture instead of just looking at it. 
Charlie

I have edited to add a couple more pictures that I am pretty sure were taken the same day and location. There is a lot more added to the story.