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
A town in Indiana, specifically in the Southern region, with Four (or five, if you count a church) schools, that sucks. It has no history except for an extremely vital Ammo plant and a bunch of stuck up arrogant "athletes" that get scholarships to IU and Notre Dame until they fuck it up and get arrested.
Stay the fuck away from Charlestown, because the only places near it are Selersburg, Jeffersonville, and Otisco.
by Colonel_Shrek February 17, 2017
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 Pokebreeder123 January 6, 2011
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 6, 2005
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 20, 2005
A really little town in the middle of nowhere that is filled with drug addicts and drunk teens
Don't ever live in charlestown indiana
by Yaydllohin September 23, 2017
When you're wiping your anus after pooping and you don't want to get the poop on your balls, you pinch the toilet paper together to get the last bit of poop.
I had sticky poop so I performed a charlestown pinch to keep clean.
by Ian[FL] November 11, 2006