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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1. A strange yet beautiful singing and acting animal often found in the urban jungle of Atlanta

2. A furious battle-rapper
1. Yo dawg, did you catch the show last night? That Cheshire was mesmerizing

2. Man, Devann was all up on his feet last night like a Katie Cheshire man- his rhymes were ill, his barbs were like venom.
by Snaphoo82 May 29, 2005

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County in England, mostly rough "scallyville" type area, given a bad rep cos of it's scenary and stupid rich people. Frequented by footballers as a place to live, but most people want to leave Cheshire as it's crap.
Home to moulton and northwich. And winsford!!!!! say no more, that place has dee bees, the club equivalent of bleach drinking , glass chewing and man-bear fighting
see (northwich) and (moulton) and avoid winsford as reasons for cheshire being "great"
by Dust E Bin September 13, 2006

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right-o folks. first off, Cheshire is a COUNTY. not a TOWN. So all you guys saying it's a town suck,and you need to get your facts straight.. RARRR..
anyways, lots of footballers have houses in Cheshire,like Wayne Rooney and some others.. David Dickinson lives here too. >.<
The towns and villages in Cheshire are Macclesfield, Wilmslow, Knutsford, Congleton, Prestbury and loads of others,it doesn't matter, the rest are shit anyway.
Cheshire is basically the most HXC county in the whole of North England, fuck that, it's the best county in the whole of England.
Cheshire is famous mainly for cheese, cats and David Dickinson, AKA the greatest living person ever, have you seen Bargain Hunt?
person 1:'i'm going to cheshire,i hear David Dickinson lives there.. i love his orange tan'
person 2: 'fo shizzle.'
by laylaMUFFIN August 26, 2007

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Cheshire may be the worst most boring town in ct, everyone in cheshire thinks they are the shit when they know not to fuck with hamden cauz they know they will be rocked. Most of the kids think they are hood when their parents make over 200,000 a year. Cheshire is also the home of Cheshire Academy probally the best part of Cheshire. Cheshire might have 10 black people and 9 of them attend Cheshire Academy, over all there is nothing to do in Cheshire the parties suck, and most of all they think they hood because they drink Coors light and all the rich girls do coke so over all its the worst town in the world with the most annoying kids and worst athletes in the enitire universe.
1.Cheshire kid: hayy lets fight someone tonight because we have nothing to do
2.Ok where you wanna go?
1.Not Hamden we would get messed up
2. Ok good idea lets mess wit Southington kids beacuse we are pussies and we wanna fight someone that we can actually win i dont wanna get hurt by all the big black hamden kids im gonna cry now!
by BOB The Great April 23, 2006

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cheshire or as the gay people of cheshire like to call it "the shire"...wow thts gay... any way cheshire is a little town next to hamden and southington ct. ..theres one way in and one way out of cheshire. there is absolutley nothing to do there. it is probably the most depressing boring town you will ever see ....besides prospect....the sports in cheshire are absolutley terrible...there town basketball leagues all play in the same place at the same. wichis in the mighty fine gym of the cheshire academy institute .. i think there mite be about 4 and half black people in the town of cheshire..... It is moslty rich white kids, and arrogant ass licks. thers a little gay skatepark were all the little white kids go to fall on there asses for everyone on route 10 to wach and laugh at. theres also a place called cheshire academy theres alot of asians and pot heads there ...dont get involved with them.....if u ever meet anyone tht brags about living in cheshire or tries to defend it .....punch them in throat and tell them to get a fuckin life u fuckin poser ... kids tht live in cheshire live the most shelterd life known ct... i think there is maybe a mcdonalds and a subway in cheshire and tht about does it for resturants ...no movie theatrs.....all kids in cheshire dream of one day moving to hamden so they can one day go to notre dame west haven or play hockey so u can go hang out and the hamden rink were all the white trash hangs out and watches the elite hockey team play ....and go ride your bike to ray and mikes and the high school thinking your cool ....thank you for ur time
"let's go to cheshire "
"no let's not "
by P thing April 25, 2006

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