Cheshire a town right next to southington This town is the biggest drinking town in all of CT. We have some of the best bud there is. We also love to fuck with southington kids. Southington kids get rocked by cheshire every friday when cheshire goes to the southington movie theater. Southington steps and then cheshire beats there faces in.
1 Wheres the party tonight?
2 It's in cheshire
2 I heard there is going to be 5 kegs this time instead of 3.
1 O nice.
by It don't matter what my name is September 12, 2004
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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 30, 2010
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Cheshire is a little area in CT which is too big to be called a town, but it's not really a county either. I'm from Cheshire, so yes I would know. We have huge sports rivalries with Southington and Hamden. About 92% of the kids smoke pot and/or drink and think they're cool. Most of the residents live in nice houses, have nice cars and are not worried about this recession. More than 55% of Cheshire is owned by the Bowman family. There are like 10 black kids, just stating the facts. Anyway the girls stay tan (not really tan, more of an orange) throughout winter and are mostly preppy. The guys are mostly preppy too; therefore there are no hot scene guys... They party a lot and have a record for the number of arrests that have been made, especially recently. The popular music in Cheshire is whatever's on the radio, and it's usually hip hop or rap. The preppy kids think its cool to be "punk" so now they are starting to wear checkered patterned shirts and converse, when they are clearly not original like the people who've been doing it for years. They are also starting to discover bands like 3OH!3, Cobra Starship, etc and claim to be fans, yet again, it's been done. The people are usually all fake except for a select few, and the mothers love to gossip with each other.
Cheshire Mother #1:so i hear johns kid got arrested for having a party last weekend?
Cheshire Mother #2: oh yes he told me all about it but keep it on the "D.L" because i wasnt supposed to say anything.
later...
Mother #1 to Mother #3 over the phone: you'll never guess whos son got arrested!!!

Cheshire Football player #1: game against southington tonight!! whooo were gonna totally kill them!!
Cheshire Football player #2: yeah mannn n after we can set another one of their cars on fire then smoke a bogie behind the bleachers...
by tinygurl1747 October 5, 2009
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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 24, 2007
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Cheshire is a county in the north west of England. It's mostly posh and pretty rich, filled with people too proud to say they're from the North.

The more affluent also love to look down on the lesser areas such as (the admittedly shit) Ellesmere port.
"I'm from Cheshire"
"Where in Cheshire?"
"Ellesmere port"
"I'm Sorry"
by Luke2002 May 31, 2020
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Cheshire is a little town in CT next to Hamden and Southington. It's pretty small, not much to do but overall a nice place to live. People keep saying the kids in Cheshire are snobs, well not all of them are, it depends on the crowd you hang out with, I'm pretty sure all towns have snobs (sorry folks but that's just how life is). Yes, the town is pretty wealthy but not all people are rich. Take me for example, I live in the tiniest house on the block, very small, living room, kitchen , bathroom and three bedrooms. I never go to the mall, too expensive and I don't have a device, unless you count the shared iPad. I'm not pitying myself, just an example. The schools are pretty good. It's small and so it is pretty quiet. All towns have their cons but in Cheshire there are many more pros. please stop bad mouthing this town, it is a very nice place to live if you hang with the right group.
Cheshire is pretty nice if you look at the positive instead of the negative.
by Chubby Waffles February 28, 2017
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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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