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.
by filmguy619 December 1, 2010
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An adjective used to describe a smile as extremely wide and mischievous, cocky, or malevolent looking--"a Cheshirian grin". Derived from several adaptations of Lewis Carroll's Cheshire Cat character in Alice In Wonderland, including the Disney version.
by Lheticus November 7, 2013
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by Lostpeace December 21, 2003
Get the Cheshire Cat mug.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...
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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