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3.
A small town in southern Indiana, not too far north of Louisville. It used to be home to an ammunition plant that was actice in WWII.
It has rather crappy schools that are trying to improve themselves with the 1:1 Program, a program that distributes one Macbook to each student. They're beginning to make some progress, but they've got a long way to go. Their mascot is the Pirates.

Ignorant, Bible-thumping rednecks abound. Beware. Also, like the rest of Indiana, they're obsessed with their sports, especially basketball.

At least it's got some nice open land out in the sticks near town. Beware of trigger-happy people who enjoy shooting anything that moves in their yard, though.
Charlestown is trying to drag itself out of the depths. It's getting there, but it'll be a long haul.
by Night-san January 05, 2011
 
1.
Pretty much the best part of Boston, trumping that shit bag a place they call Southie. Its where the real Boston Irish come from and where nobody will fuck with you. Outsiders hate it because they know there not welcome, espcially cops. Unlike Southie, Charlestowns never produced any rats, and thats why the cops hate it. In other words, its God's country! The people who live there, called "Townies", have always taken care of eachother. They all feel a real sense of community with one another.
FBI Agent 1: Think we should canvass the neighborhood, ask if anyone saw anything?

FBI Agent 2: You do realize we're in Charlestown not Southie, right? No one here will talk!
by Crazykid50 March 23, 2011
 
2.
A small, highway-side town that is largely dominated by the Charles Town Racetrack and Casino, which serves as a hub for all those involved in the horse racing industry, a very tight knit group of people. If your not into horse business, (betting, training, riding, owning, etc.) not much reason to stay. However, exploring the surrounding area offers some gorgeous West Virginia, picturesque, natural lands much loved by outdoors-y types, as well as the beautiful Shannandoah river. Also check out Harpers Ferry, lots of history, exploriing, and hiking around there.
There was hay in the streets, manure smell in the air, and an Applebees. Welcome to Charles Town
by Lil' Georgie December 05, 2010
 
4.
Charlestown is the white slum of Boston. Theres no way out.
look at the other definition of charlestown, you really wanna live in a place named after such a thing... damn
by onthegrind November 19, 2005
 
5.
A term used for a school that is cheap, stinky, ugly, uneducational, and depressing.
"There are many Charlestowns in the United States."
by Amanda February 05, 2005