As I was raised in this God-Forsaken Town, I think I'm fairly qualified to write about it.
Winchester is the County Seat of Clark County, smack dab in Central Kentucky, real close to Lexington, KY. It's a small town with a few cool things, like a 9-Screen Movie Theatre, with a local pizza joint called Sal's Pizzeria in the same little shopping center, across from McDonald's and right off the Interstate Exit.
Living in Winchester is a highly practiced art, where by in order to do real well one must be in the Country Club, or be close friends with people in it. The County contains many elementary Schools, 2 Middle Schools, Clark Middle and Conkwright, which has a magnet school built in, and one fucking overcrowded High School called GRC.
The plus sides are-
-nifty keen park
-pretty enough downtown
-three chinese restaurants
-a Super WalMart
-plenty of places in the county to get on in the woods

Down Sides-
-most of the people