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 05, 2009
Cheshire is a rich town in CT. Half of cheshire is owned by the Bowmans, a overly-rich family who isnt afraid to show off their money. In total, there might be 4 black families in cheshire, who make more money than the rich white families. Almost everyone in CHS smokes weed, and drives some kind of expensive car. Cheshire does have some nice parties though, and most people arent greedy with their bud, so over all cheshires alright.
Cheshire Black kid: Hey, my parents made 1.2 million this year, how much did yours make?

cheshire White kid: around 700,000.

Hamden kid: uhh.......mine only made 60,000.

Cheshire kids: thats ok, you can come with us, were gonna buy lots of bud with our parents money

Hamden kid: Cheshire kids own!!!
by Teh bishz0r July 10, 2008
(n):
1. One who mimics others for social attention or personal benfit

2. One who is deceitful in their use of style theft from another individual for sake of social attention or benefit

3. One who robs ideas from another to further themself in social ranking and/or status

4. a social parasite
"{persona} said that exact same thing only two minutes ago, and now {personb} is already recycling it?"
"I know, he's such a cheshire."

"No one is ever going to like you if you continue to be a cheshire."
by push.tyber March 19, 2005
Contrary to other definitions, Cheshire is in fact a well-heeled and well-to-do county in the North(ish) of England. It is where people own Range Rovers, cows and occasionally large expanses of land. Also home to many Manchester United footballers.
"Cripes! Look how flat it is and how many cows there are. We must be in Cheshire."
by Whippet May 29, 2005
Yes it is a wealthy town in Connecticut, but nothing compared to fairfield county. Contrary to what most believe, most residents do no flaunt there money, but some do. There are plenty of large expensive homes, but there are alot of small, medium sized homes. Many people do, in fact, have second homes (the cape, vineyard, vermont, florida) and many vacation any chance they get. But you have to understand that this is not the case for everyone in town. The stereotypical cheshire kid is polo popping and has a nice car, but again, its not everyone. College is big...very big. A schools reputation goes a long way in this town. Ivies and mini-ivies are common, but a ton of kids go to uconn. 98% of CHS students go on to college.Schools in town are very competitive, if u have a B average (3.0gpa) you almost always in the bottom half of your class.Parties are also a big thing because theres nothing else to do. BMWs, Mercedes, Lexus, Land Rovers, and so on are not uncommon, but there are plenty of chevys, fords, and jeeps.Snobbery is something you have to get used to, but not everyone is a stuck up. My point is is that cheshire is not filthy rich. There are plenty of average familys who work hard and live modestly. Its a great town.If you wanna see rich go to fairfield county.
Cheshires the place to be
by mtopps March 22, 2009
A pretty wealthy town in CT about 20 mins north of New Haven. Its not as fucked up as everyone thinks it is. There are plenty of people who aren't filthy rich, but there's definitely enough rich people and it gets richer and richer every year. It pounds on scrub towns coughsouthingtoncoughhamdencoughcough. Parties are pretty sick also. Drug use is becoming less severe. Mercedes do not roam the streets, but there are enough of them.
cheshire ct
by chettomonster January 19, 2009
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
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

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