Westport Island

1. Island in south-east Maine really dang close to the border. Wicked scenery, ten miles long, one mile wide, solitary gas station with fraggin' expensive coffee filters if you run out on Christmas Day. That and a firehouse. Not much else, really.

That last town we went through was so small it coulda been Westport Island.

by Mainer in Exile January 12, 2009

Westport Republican

A Connecticut person who professes to be a supporter of the Republican political party and its ideology yet tends to vote for Democratic political candidates and to side with the Democratic political party on political, social and economic issues.

My friend claims to be a Republican, but he voted for Barack Obama for president. He is a Westport Republican.

by lawyer63 September 24, 2011

Westport, MA

A little town in Massachusetts on the coast, i mean really small. Pretty rich place in some areas and we get some vacationers here like Harrison Ford and Tom Cruise might have a house here. Every one shops at Lee's to get food which is super overpriced. Most teenagers work there too. Everybody jerks off to the WHS basketball team but were pretty ill we make it to states every year. Theres a shit load of drugs here and even mroe white people who want to buy them. Overall a great place to retire, and a shitty place to raise your kid unless you want him to be a burnout. Also known as Cowtown, god only knows why we only have like 3 farms here..

Guy1: "I live in Westport, MA."

Guy2: "Where the hell is that?"

by ballsintheface8 December 17, 2008

Westport High School

the most horrible high school you can possibly go to. there are no hot guys and all the girls are sluts. more than half of the school does drugs, and the other half goes out and gets drunk every weekend. most of the teachers there are total bitches that dont give a shit about the students. the subs drink as much as the kids do, and theres never enough food at lunch. the sports teams have to team up with other schools just so there can be sports teams, and the town its located in is in the middle of nowhere. if you move to westport, dont go to westport high school.

"where do you go to school?"
"westport high school"
"dude i hope you dont get me addicted to weed or something"
-.-

by th3r3alslimshady420 February 20, 2012

Westport High School

a high school in the shittiest town to live in.... westport mass. Everyone is shady and two faced and everyone loves to talk shit. If you dont want your kids to become raging pot heads dont school them at westport high in that case any school in the westport community schools department . also fall river kids are usually not liked and they look weird an ecaple is the sea cucumber from spongebob. the teachers are not only as big of pot heads as the students but are very bad and do not know how to teach. the school lunch is horrible and is usually served cold. the school also looks like its going to colapse just looking at it

westport, westport comunity schools, westport high school

by crazypothead June 2, 2011

Westport Mafia

a organization/gang of white trash trailer park boys go around acting hard and wanting to be cool. Almost all using or making meth and giving it to the militia.

Person A: " Dude don't go over that Westport Mafia territory."
Person B: " Ah shit them mofos hard as fuck."

by MrLahey January 3, 2018

12. Westport

A mainly rich population. Houses overly priced for who knows why, some of them are tiny and crappy. Kids are mostly sterotypical and own multiple pieces of designer clothing. They also don't know the true meaning of poverty, but think they are so terrific when they 'help out' in some way shape or form. Unlike most other people say, Westport teenagers don't all go to ivy legue schools. Only about 25, more or less, of the top students make it.

Although Westport is a great place to grow up, I hate it. Especially when kids from other towns think I'm spoiled. For the record, my parents went to the college of charleston, not some big ivy legue school, and they know what it is like to be poor. Since they do, I have to work for just about everything, or I won't get it. Oh yeh, and I hate designer clothing, I don't own one single peice of it.

by anonymous teenage girl July 18, 2005