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2.
Winchester, aka WinVegas or Wincheesey is the center of the drinking culture on the east coast. Because all parents are rich CEO's/lawyers/doctors in Boston (which is wicked close) they are either work-a-holics or alcoholics, perfect for the party scene. The work-a-holics leave empty houses for their children, having either a business meeting, jetting down to the "islands" or some other exotic vacation locale, while the alcoholics supply booze for their underage children. Teenagers are rich, and pretentious, and the future of America. We hate all of our surrounding towns, especially woburn, or "the woo", frequenting their sporting events only to yell "don't drink the water". We support all boston sports teams, sox, pats, celts, bruins, and probably have season tickets to all of them. We pop our polo collars, and wear or seven jeans, and will buy off the police officers who catch us having our "ragers" at open houses or in the woods at the "fire spot" or "the rock" if we couldn't make it to whipple hill. This town is the shit, and we know it. Wincheezy up, Woo town down.
Oh, she's rich? Her parents own a company? She's wearing expensive jeans? She has a summer home on the cape? She loves the Red Sox? She can drink more than the average 40 year old male? She must be from Winchester, MA.
by youwish February 24, 2006
 
1.
THE REAL WINCHESTER: Winchester, or Winchedda, is a seemingly serene and quiet small town that radiates a familiar, “everybody knows everybody” type atmosphere. Down town Winchester, often referred to as dt, is quite a welcoming sight with its beautiful scenery and charming stores such as The Dugout, Joe’s Main Street Pizza, and Video Horizons. Winchester’s residents are extremely wealthy, privileged, and selfish, because their abundance of money never gets put back into the actual town itself. The high school is extremely run down and was designed originally to be a prison, making it quite a depressing confinement. The school never seems to have enough teachers or resources, yet its students’ families are drowning in affluence. At night the small town community practically shuts down, without a car in sight and the substantial population of senior citizens tucked cozily into their beds, sleeping soundly with all the financial comfort imaginable. Converse to the outward appearance of a subtle and lackluster nightlife, teenagers of the town drink like mad and party heavily. Growing up in an atypical society where parents grow accustomed to their children underage drinking and devote their efforts into preventing drunk driving and brainless actions involving encounters with law enforcement, the typical kid begins drinking at about 8th or 9th grade, becoming more routine and excessive with it through high school. Motivated by the lack of enlivenment of their town, the high schoolers throw massive parties, or “ragers”, whenever dim-witted and trusting parents leave town, turning their home into what is known as an “open house”. Parties are frequent as is the practice of alcoholism. Intoxication is heavily glorified, fueling most teens to drink enormous amounts of alcohol each night of the weekend. When there are no open houses, social gatherings are arranged in the fells (woods). Kids flock to well known places such as The Jumping Rock and Narnia deep in the forest, havens far from the reach of cops. Most every kid not only drinks but also smokes weed because of its ease of access. Somewhat ironically, it’s much easier to attain than alcohol. “Wake and Bakes”, when kids smoke before school are very popular along with smokeless tobacco. Athletes and jocks are expectedly placed on somewhat of a social pedestal, but in no comparison to most schools. Rarely will you find a stereotypical jock lurking through the halls shoving freshmen into lockers; that just isn’t Winchester. The football team is notorious for its mediocrity (generously put), however lacrosse and wrestling do extremely well. The majority of the student body is intelligent considering it’s a public school. The high school slang is incredibly unique and constantly changing. Doing smokeless tobacco is often called packing a dip, lip, bomb, ding, dinger, and even something as simple as packin’ a guy. Marijuana is often referred to as weed, pot, binger, ripping bong, and ripping bing.
-How many kids are getting down on the 30 tonight?
-I think 4.
-That's terrible. That means 2 kids will get 8 beers and 2 will get 7.
-Whatever, it's Natty Ice, higher alcohol content. Every 3 beers is 4 of any other brand of beer in Winchester, MA.
by OneLove1 July 07, 2009
 
3.
A town north of boston that is filled with kids who like to get drunk at a house, or in the woods wether it be the firespot, rock, golf course, whipple, etc until the cops come and half ass chase us. The pot heads in this town also happen to be the smartest of all kids unlike those commercials that say weed makes you dumb.
Its friday night lets go to Y***** S*** get some nati ice and party in Winchester, Ma
by wincher September 23, 2006
 
4.
A town that goes the hardest when it comes to drinking and partying. Home of the Sachems and passionate singing group The Boys World Premiere. House parties are the center of the social scen, whether its Dave's week or the hiring of strippers and kegs. Everyone goes to prestigious colleges but when it comes to it, the crews at home take the cake. Everyone's down to get fucked up cause Winvegas never dissapoints. We drop our "r's, and live the life of reilley. Nothing beats it when you cross the local spots like ginn field, Norwood st., or even Nike. Winchester has that sting that makes us 4 miles north of Boston...
You know your from Winchester when dips food and beer are the diet
by Big Time Stretch July 06, 2011
 
5.
Ok so Winchester is a town close to Boston that is home to very rich parents with big houses and rich children. There are some people who aren't rich and just live there for the schools and people usually notice. The town is so boring there is nothing to do but spend their parents money or drink and party. So of course they drink and party. Winchester is the sort of place where if your in, say Main, and you tell people you're from Winchester, they'll look at you funny and automatically assume you're a rich bitch, which 65% of the time s true. Winchester is known for its abnormal alcohol and drug use, despite the schools' constant reminder not do drink and not to do drugs. The schools are really really really good and an A in Winchester is good in a college's eyes. There is a ton of pressure to take AP classes and do well in school. The teachers usually can't even afford to live in Winchester. If you're from Winchester and people don't know you very well they will probably judge you for living there. Every kid in Winchester absolutely HATES Winchester with a burning passion because it's so boring.
by Foodyum April 28, 2013
 
6.
Winchester is a town in Massachusetts about 8 miles north of Boston. The kids who live in Winchester usually have very rich parents and therefore they can get away with anything. People from Winchester are actually more obnoxious than the richer towns surrounding it (Weston, Wellesley, etc...) and try to make it seem like they are much better. They like to brag about how close they live to Boston because they think it's cool. And when they are around people from out of town they often say "wicked" more than they usually would -which is never- just so that people will know their proximity to Boston.
"Hey where are you from?"
"Oh, I live wicked close to Boston. Like, closer to Boston than Weston and Wellesley and a lot of other towns. I'm actually like wicked rich and I have a lot of parties, and they're always wicked fun. People always have a wicked good time."
"Oh. You're from Winchester."

If they use the word "wicked" multiple times in one sentence then they're from Winchester, MA.
by anonymous472389 April 11, 2010
 
7.
Winchester is an interesting suburb to the northwest of boston, about fifteen minutes away on the commuter rail, and home to a shifting teenage demographic which varies over time between independent and friendly and alcoholic and hateful, although the alcohol is pretty consistent, as is the jockness, but as much as they change they're always just the same as their parents - rich.
Some interesting people have appeared here, though.
Slang is unique. Most words end in izzy. Worthless people are called vus. Like if someone starts a fight, freaks out, backs their car really fast into someone they don't even know's car, then drives away, people will call after him "vuuuuuuuuu" before bolting from the Winchester Police Department. Or is someone gets heartbroken, and sends naked pictures of his exgirlfriend to her future professors at the college she's planning to go to before she gets a restraining order on him, the community will have labeled him a "vu" by nightfall.
Very critical town. No one knows where this old tradition comes from.
Come visit! Exit 32b on 93!
I lived in Winchester, MA for nineteen years and wasn't forced to deal with too many vus.
by lifelongwinchester October 05, 2005