Hi: For some time now, I have been typing Barry Co., MO, newspaper items for the years 1890 through 1913. And in among the listings there were several Calloway names. You might also check for Callaway to see if there were any other spellings given.
When I have the project finished it will include up to and including 1921. But there are already a lot of papers listed and tons of information that will interest researchers of Barry Co., MO and the surrounding areas.
There is a search engine on the front page, and you will probably need it - but if you just want to walk through them, then just go down the page and you will see listed the Barry Co., MO Newspaper project.