I've hunted Kentucky the last 7 yrs or so. The bow season starts early September and you may also use a crossbow from 1 October through the early two day M/L season (this season's was mid October the 16th & 17th). The gun season (rifle) is tied to Veteran's day and is two weeks and three weekends long. This season coincides very closely to the peak rut time IMHO. My Kentucky buck was actively chasing when I took him this year (cull buck). There is also a late M/L season in December, one week and two weekends. Bow ends in early January.
I hunted Indiana for the first time this season, the Florence, Indiana area. LOTS of nice bucks in this area, Switzerland County. Apparently this county leads all others in big bucks and total number of deer harvested. Two week gun season (possibly being shortened). Shotgun, M/L or rifle shooting pistol calibers (or wildcats) up to 1.6" (case length) or thereabouts. Pistols are legal, but out of state must possess a permit, I believe. Pistols may fire any cartridge, even rifle chamberings, such as .35 Rem, 7/08, .308 etc out of Encore, etc. I hunted with a .44 mag Handi Rifle. The area I hunted was pretty thick with 100 yds being a long shot, except overlooking fields. My 135" deer was very big bodied, but nothing special rack-wise at the check station. Lots of nice bucks in this area!!
Hope that helped some.