Not sure what part of the Midwest you be near. There is a renaissance Festival near St. Louis, a place called Wentzville Which takes place the last 3 weekends in May and first weekend in June I believe. They had a pirate show called "Captains Outrageous" . And there be various pirates roaming the grounds also. I think they also had a pirate ship stage. KCRF in September and October, usually has a Pirate Weekend and we have the Jolly Rogers (they have a great show...singing and joking)on a pirate ship stage that is bigger and better then St. Louis. KCRF has been going on near 28 years and St, Louis is only in its 5th year. :) There are all sorts of little Ren faires all over the Kansas, Missouri, Iowa, Oklahoma area, some only a weekend long and some better then others. Check http://www.faires.com/ . They have a lot listed. Scarborough Faire near Dallas is a great Ren Faire also, with a goodly amount of pirates, and I can't remember there pirate group, my hubby said it was "The Bilge Pumps". We visit Ren Faires on vacations, so have visited quite a few.
Huzzah!!
Candy