Thread:Project:Support desk/Automatic content import of .txt Files into a Wiki System. (Bot?)/reply

You could use a short shell script (or batch file since you're on windows) combined with the edit.php maintenance script to easily go through the directory and import all the text files

You could also probably create a bot to do that. You may want to check out w:Wikipedia:Creating a bot (Some of that is wikipedia specific, but much of it is general).