A somewhat small town in Northwest Indiana. It consists of some pretty cool people, and lots and lots of corn. It is also considered a suburb of Chicago. It has some nice beaches, even though Michigan has better ones on lake Michigan, and it is way way way too flat.
Hey! where are you going? I'm going to Chesterton.
by CMLB July 11, 2008
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Chesterton is a small town in Northwest Indiana, a little less than an hour away from Chicago. The towns buildings are mostly fast food related, with the exception of Broadway, a street full of small town businesses that are never hiring. The high school is full of mostly druggies, dirty kids, and skanky freshman girls, with some rare relatively cool people as well. The army is always at the high school school, which is all the rage amonst the dirty kids, but most normal people find it extremely irritating. It's no surprise that most kids are druggies, considering the only things this town has going for it is a tiny ass bowling alley that smells like cigarettes and a put put golf course.
Person 1: Wanna buy some drugs and hit on some skanky freshmen?
Person 2: Sure, let's go to Chesterton.
by Senior Burrito January 29, 2011
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Chesterton is a small town in Northwest Indiana full of corn and dirty kids. It is less than an hour away from Chicago and 20 minutes from the nearest Walmart. The school system has money for an astro-turf football field but not enough money for paper. A common hobby of most teenagers here is doing and selling drugs when they should be focusing on their education because they are higher then their grades. This town is getting worse then Portage. Please help.
What do you think of Chesterton? Man, that place sucks.
by Chestertonsucks. January 12, 2012
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Chesterton is a small town in Northwest Indiana. It's ruled by corn fields and is right by the great lakes, but everyone here goes to Florida for beach days instead. Chesterton is the local hick central; complete with confederate flags on hoodies, students who ride tractors in, and a school board that'll defend students who call you a faggot. Each day you go to the high school you have to wonder whether or not you'll see someone vaping in the bathrooms today. Other than an old entertainment center that has a color scheme crisis every 2 weeks, and a water park that violated health codes and has been shut down since (both of which aren't even actually in the town), there's absolutely nothing here other than local restaurants and shops.
Dude, you came from Chesterton? I'm so sorry.
by dumbsapphic June 22, 2019
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Describes the act of one man or woman defecating on the chest of a man, preferably with a very hairy chest.
"Bob just gave Hubert a giant Chesterton."
by copey July 21, 2006
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Chesterton is located in Northwest Indiana. Home of a kick ass swim team that always beats the skanks and douches at munster. The swim team has 15 straight conference wins, 12 straight sectional wins, 2 state titles soon to be 2 more due to the large freshman class that came in 2010. Go trojans!!!!
Chesterton, Indiana, home of a more premier swim program that beats munsters "premier" program.
by Trojan-territory November 22, 2011
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You wake up at six in the morning to go to a building which resembles a prison located in the Hopkins area where a compulsory 4 years of a teenagers life are wasted.

While strolling along the corridors of CA you may come across some of the following paracites:

The Homeschoolers. They are rare, overly sheltered humans who lack the ability to socialize with humans other than their mom or one of their 15 siblings. If you say stupid they will immediately drop their things and find a teacher. Unless that means not being 4 minutes early to class. Because that’s the most important thing.
The Quiet kids. You don’t know if they are also homeschoolers, or just mentally coo coo. It’s quite rare to walk past these kids without being stared down until you turn the corner and are out of there sight.

The somewhat-normal kids:
These people DO KNOW how to socialize, they understand there’s more to wear than farmer jeans and polo shirts, and oh yeah. They have Cell-Phones. Which is quite rare until Junior year for most people at CA.

Finally, there’s the special individuals. They are either 11/10’s and don’t belong in a sh*thole like CA, or they clearly the superiors. Pretty much what normal high schoolers should be. But they are hated by the teachers because they are not sheltered enough, and they might “spoil” the other future seminarians.
**Meeting someone new**
“Hey what school do you go to?”
“Ohh uhhh... a private school in Hopkins :)”
“Oh what’s it’s called”
“Uhhh it’s really small you probably don’t know it”
“It’s okay try me.”
“Okay... Chesterton Aca—“
“HAHAHA NERD. YOU GO TO CHESTERTON ACADEMY??”
by irregularforcircles March 9, 2021
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