A decent sized town in CT in New Haven County where about half the population is rich and the other half is upper middle class. Several of the athletes at CHS are really good at sports, and some of the people that live in Cheshire aren't too bad, not as bad as people that live outside of Cheshire make them out to be, but it depends on what kind of crowd you hang out with. Also, as rich as the town is, it's nothing compared to like Greenwich, New Canaan, Ridgefield, or Darien. While their isn't too much to do, Cheshire has plenty of restaurants, including a McDonalds, and it has a bowling alley. Plus, it's near malls, movie theaters, New Haven, and Lake Compounce, so overall, Cheshire's an alright town.
Go Cheshire High Rams!
by filmguy619 November 29, 2010
To question someone to the point of pure exhaustion.
He was going to get the sale, but pulled a Cheshire and questioned him to death.
by Swansond January 10, 2014
Everybody thinks that our little bedplant town is pretty fucked. Well those b*tches are wrong. Sure we might have some money, but that doesn't make us complete dicks. Thanks for the bad rep. and the pathetic rumors. You guys are terrible people. Go to Hell. ;)
Cheshire has money, but we aren't stuck up snobs.
by smiles333 February 12, 2012
A pimpass billygoat that eats tapeworms and nails for breakfast. Afterwards he goes skinny-dipping and then jogs a mile to the nearest candyshop to poop on thier butterscotch and piss in thier cornflakes.
What a cute little cheshire.
by Beast Qoc April 02, 2011
Best county in New Hampshire! ...er, not really...
There's a lot of hicks around Winchester and Westmoreland, but over on the east side, you get a lot of wicked rich people, mainly in Dublin. Apparently there's a lot of famous people with summer homes on Dublin Lake. Mount Monadnock is at least partially in the county, and we have really pretty scenery, which attracts loads of tourists over summer. Home of the Cheshire Fair, which is actually kinda lame, and the Swamp Bats baseball team.
NH person: "I'm from Cheshire County"

NY person: "Wut? I thought that was some shitty town in Conn..."

NH person: *slaps forehead with hand*
by Olli Vee April 06, 2010
the classical belief was that cheshire was a type of smile. However, urban slang used in the bad ass suburbs of hertfordshire uses the expression to express their distaste for someone. It becomes a derogitary term usually used for a snitch, e.g. a grass, rat, tatletail, fibber or ragbag
Don't cheshire on me, or i'll tell veryone your a cheshire
by mad ali May 12, 2005
A really rich town in Connecticut that belongs in fairfield county. Everyone's parents are either CEOs or VPs. All the guys wear polos from lacoste or ralph lauren and all the girls have lots of accessories from chanelle, prada, dolce gabbana, and coach and loads of jewlery from Tiffany and Cartier. Nobody knows what a knockoff or a sale is and most of the houses price well into the millions. Everybody owns at least 3 luxury cars. Everybody spends their summers in Cape Cod, Nantucket or at a snobby Country Club where they play golf and tennis. And everybody is white.
I wish i lived in Cheshire cuz then i'd be rich.
by J. J. Smith November 23, 2007
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