a. noun
A small town on the East coast of Virginia, located on the Chesapeak Bay.

Mainly habbited by guinea bubba's, red necks, wugs, or wiggers. Because of this stereo type of people and excessive Inbreeding between families, Gloucester's literacy rate is very low. Not allowing for upper standard events to take place and/or attractive people to evolve. On a town rating by men and women. 8%=Fuckable and 92% of people in Gloucester are Butt-Ugly. When compared to the Local City of Williamsburg neighboring Gloucester; 89%=fuckable and 8%=Average 3%= Butt-Ugly. A big difference in this small town.

b. A small town where there is nothing to do, other than to go to school or skate down the rocky roads and bust your ass on rocks.

C. A Favorable place to attempt the Water sport of Wakeboarding. Because of Gloucester calm waterways and warm water.
Wigger 1: Yo, you don't fuck wit me! I live in that busted up trailer park called Sea Breeze.

Wigger 2: Yeaaa yo!, you gots ta pack heat round thur. Oh shit my BB gun broke...I'm fucked.

Betty Sue: Hey dawling! com'n o're here and gimme some loving. You talk to your uncle...ahht! I mean brother, nooo or is he your daddy? well, you talk to him yet?

Little Guinea Boy: heehawww! what?? ahh I dunno we don't have a phone. And he was making sissy scream last night like he use to with momma.

Kevin The Skater Boy: Mannn FUCK these rocks! I keep busting my ass everytime I try to do an ollie on these stupid fucks! Fucking cheap ass gloucester transportation.
by Kevin Baines March 6, 2006
Get the Gloucester mug.
A place on the north shore of Massachusetts where 15 year old girls go to get pregnant in large groups, with a binding contract, or "pact".

Also, it shares an island with the beautiful seaport town of Rockport.
Guy 1: Dude, my girlfriend and I are going to Gloucester for the weekend!

Guy 2: O shit dawg! Don't let her talk to other girls!

Guy 1: Why?

Guy 2: She'll make a pact with them to get preggers!

Guy 1: OH SHIT!
by SAYInWhaT May 16, 2011
Get the Gloucester mug.
The official town of whores. Just ask the 17 girls... sorry, whores, who got pregnant in 2008. Not only did they get pregnant, but they made a pack to get pregnant so they could raise their kids together. Aww, how sweet... except... they're in high school and middle school.... awwww....
Gloucester Girl: Hey! I have a great idea! Let's all get pregnant and raise kids! Won't that be fun?
by xoxorokkixa**xo July 14, 2008
Get the Gloucester mug.
A very crap place to spend you life. Three words: don't do it! it is a shitty place to spend your teens with hardly anything to do until you find out about the guildhall and go to it's gigs!!
OMG! My second gig in a month!!
by helena venom April 25, 2005
Get the gloucester mug.
The craphole where people who don't want to be their go.
Fuck you No way i'm goin 2 Gloucester. I got sense man.
by Brendan ;-) April 22, 2004
Get the gloucester mug.
a bitch city on the north shore with people who think they are affiliated with the bloods. a city filled with people who think they have it hard, and are sadly mistaken.
231 cities/towns in massachusetts have more crime, and poverty than gloucester.
by kingpin2 July 5, 2007
Get the gloucester mug.
Shittiest school in the UK. North Korea but it’s a school. Literally a prison camp. U get a detention if ur shirt ain’t tucked in properly.
Bob: I hate my school.

Jeff: At least you don’t go to Gloucester academy.
by TheTaxMan420 July 11, 2022
Get the Gloucester Academy mug.