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1.
Shitkickers, Plaid, Whores, Drugs, &The best people you will ever meet.

Teenagers run this town.
Person 1: Have you ever been to Bennington?
Person 2: No, but I heard it sucks.
by hipsterwhorefromvermont January 10, 2011
 
2.
One of the most mundane towns ever. Bennington has many things to offer... such as hicks, whores, and potheads... Yep. B-town sucks. It's pretty, though.
Just go to Bennington for at least 5 minutes and I'm sure you'll find an example of your own.
by OrigamiPeacock April 02, 2011
 
3.
Crapshite USA
It's a crapshite of a town that Bennington.
by Lolalocka October 15, 2008
 
4.
Cows, Farms, lifted trucks, and Carrharts
In Bennington we take our lifted trucks down to the farms and tend to the cows, well we wear hot ass carrharts.
by Missing the stars October 15, 2008