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2.
Pittsfield is a medium sized city in Massachusetts. Pittsfield is known as the city that crashed like an elephant through a glass basement. Pittsfield is THE “anti-mixing pot”. About 80% of its population is white, but about 79% of that number are either insane, stubborn old people who refuse to let go of the once prosperous city, or insane, stubborn young people who insist on making the city progressively worse. Of course, the old-timers have some trouble adjusting living in between one house testing hand guns and the other cranking hip-hop music on full blast and bass. Most policemen don’t take them seriously, though, so their cries of help are usually ignored. Pittsfield does consist of whites, but only the kind of white people you fear having to work with (i.e. Crazy hicks, overzealous white gang members, abusive poverty stricken parents with too many children, etc.). If you’re a high school student, chances are you either attend PHS (Pittsfield High School), or Taconic. If you’re really looking for a good time, though, maybe you can roll on by Miss Hall’s School for girls and see some bored rich girls mooning you on the side of the road trying to suck some measly entertainment out of there isolated lives. North Street is unique in that it’s one of the only places in where you can get weed, a hooker, a bike, power tools, and latex rubber masks all in the same thirty square feet. You can go on and swing down by Palmers variety store. Take a little look towards the back wall. There you’ll see high schoolers and/or middle schoolers getting stoned, laughing there asses off, and eating candy all at once. You’ll sometimes see marijuana stuffed in lockers at school, but of course the principals are too arrogant of their schools to run a dog test. Basically, Pittsfield is a town run by stoned kids, and occasional gang wars.
…Dude, and then the b**** was like, class you need sh**, and I’m like f**** that…
-Jittery male Pittsfield High student

You rotten brats! Get the hell out of my driveway! -Over protective senior citizen of the “good old times”

Just take the extra change and leave, please! -Nervous Elm Street shop cashier
by Squiver November 12, 2005
 
1.
A small "city" in Western Massachusetts that used to be a hopping blue collar place, but the biggest employer starting closing down over the past three decades and now the brainiacs have decided to ride the "art" horse to death to bring tourism, which only results in clogging of the streets with dumbasses from Florida, Jersey, Connecticut, and New York who apparently still need driving lessons or are just THAT MUCH OF AN ASSHOLE to make you late for work EVERY DAY no matter how early you leave your house. And the art is stupid.
"I'm sorry I'm late for work... had to drive through Pittsfield to get there and almost ran some freaking New Yorkers off the road in a fit of rage."
by Resident Hottie June 17, 2008
 
3.
The largest city in Berkshire County, Western Massachusetts. Despite the county’s reputation for seasonal beauty/high-end tourism, Pittsfield is a relative wasteland--the result of GE closing, the largest employer of locals for decades. GE operations left behind PCBs, contaminating land/bodies of water. This has had long-term effects not only to the economy, which has exponentially crumbled, but to the biology of the city’s residents as well. Mutations have increased in incidence, with the downtown populated by mutants, street ghouls, retards, sex offenders etc. There are many Rascal scooter riders who may be missing legs, and ride slowly in traffic--though many can walk. Some of the to-be-demolished buildings of GE still stand, and young people enjoy drinking and breaking into the various condemned/abandoned buildings around the city. The youth culture also has a musical scene of punk rock/hardcore shows, where kids mosh to bands they think are somehow legendary. There are many trashy bars to drink, find cocaine, be attacked by Hells Angels, or get stabbed/shot. In an effort to “revitalize” the streets, hipsters from Brooklyn and elsewhere have recently infiltrated the city under the guise of creating a renaissance--by promoting amateur art, elitist local businesses, and pretending that baseball was invented in Pittsfield. Meanwhile, the original population of mutants continues to live jobless and/or addicted to crack.
A woman who allegedly intended to artificially inseminate her wife with her brother's semen using a turkey baster has been charged with domestic assault and battery in Pittsfield.
by mighty mutanimal April 12, 2011
 
4.
Pittsfield Illinois. Home of the Pittsfield High School Saukees. Known for the football teams 64 consecutive winning streak. Also Known for its Hunting. Pittsfield Sits in Pike County. A beautiful place to visit... Pittsfield is the home town of actor Ryan Carnes.
did you see ryan carnes from Pittsfield on tv tonight getting it on with another man?
by pittsfieldian August 06, 2009
 
5.
pittsfield is located in western mass, central area. pittsfeild is known for crack and gang affilated people wandering the streets aka the bloods..anyway besides that part of town pittsfield has very very nice houses and some nice neighbor hooods, basically your either poor or rich..not really an im between, the rich teens in pittsfield are usually crazy, all they do is party, drive in there fucking nice ass cars (d r u n k ), go to school drunkand did i mention H I G H as shittt? and over all there just hooligans, as for the weird kids they sit home and play wolrd of war craft or ufc fighting game, idk. but pittsfeild is a nice place with the most congested dunkin donuts in an area, 150 feet away from where ever you are standing there is most likeley to be a dunkin right there. besides the gangs,crack and crazy teens, over all pittsfeild is boring and usually nothing to do so pittsfieldians usually travel to albany ny which is 1/2 hour away, they do to Sneakys, to get there party on, or they will go to Umass or Springfeild College or Seinna to party with there graduated friends..wow, reallly this is what the pitts are about
pat : yoooo im rich lets smoke an L

mike: nahhh yo i want crack

pat: ighhh i will whip down to the pittsfield real quick
by fuckkkmeharder June 14, 2009
 
6.
City in Western Massachusetts, Very central town, Two hours to Boston, Three to NYC, its small and diverse, 3 rival highschools ( Taconic, PHS, St.Joe )
Taconic-chill PHS- reject gangsters SJHS- nice,private school, with crazy,partyin kids, aka best school, Pittsfield AKA PITTY or The Pitts is a fairly large town in which has various sections of beautifulness, sexyness, and wtf-ness. Pittsfeild is known for having ghetto areas, and also known for having some of the illest houses in the 413. There is really nothing to do at all in this town, so teens usually end up drinking,smoking and the rich kids end up driving around in there insanley nice cars while intoxicated. Unfortunate but true.
Mark: Hey lets go to Pittsfield!
Dick: OKAY! since its better than here, LETS GO!
by mmmmmmhmmmmmm March 19, 2009