Urban Dictionary is not for the faint of heart.
It’s the go-to website for definitions of modern slang like “Eskimo brothers” (don’t ask).
But it’s also got a page called “My City.” The user-generated descriptions of Westport are not — how shall we put this? — flattering.

Are Westport kids spoiled rotten?
“A gorgeous town ridden with filthy rich people that have so much money that they have nothing better to do than to drive around in their luxury cars and spoil their children rotten,” the 1st entry begins.
That’s earned nearly 500 thumb’s-up votes so far. And it’s the 1st thing readers — some of them potential home buyers? — see when they search for “Westport.”
Westport kids, the entry continues, “get either a Range Rover, a BMW, or a Lexus when they turn 16, get incredibly drunk and stoned at least twice a week.”
The next explanation of Westport begins: “A beautiful, mid-sized town in Connecticut. It has great shopping areas and vast estates….Some waterfront homes can cost in excess of 20 million dollars.”
Westporters “do not feel the need to wear their wealth on their sleeves,” this entry reads. “It is a great place to live and a haven for Judeo-Protestant wealth.”
By the 6th entry, someone has written:
The greatest town on earth. Everyone is really nice. Sure some people are snobby but there are people like that in every town….Just because alot of people have boats and huge houses doesn’t mean that they are lazy. On the contrary it means they worked hard to make the money and they deserve to use it in the way they want to.
According to the next contributor:
The kids here do massive amounts of drugs (weed, blow, and an occasional E pill) and party extremely harder then most other suburban communities. Despite the excessive partying these kids have seen the world three times over and are some of the most cultured and classiest individuals around.
Young adults between the ages of 16-25 basically live in a drugged out haze of parties and sexual favors. Kids quietly compete with one another about who has the biggest summer home, who goes to the better college and who can amass the most materiel possessions.

Plenty of Westport teenagers are NOT uncaring, spoiled materialistic brats.
The next writer is “extremely offended” by those characterizations of Westport. “Not everyone gets drunk all the time and smokes pot.” There “aren’t too many” people with expensive homes and boats.”
And, “not everyone is a complete jackass and extremely materialistic.”
The good news is that most of the comments are several years old.
The bad news is that for everyone looking up our town on Urban Dictionary — and it is a very popular site — this is the “Westport” they see.
In 1960 when I was offered a job teaching at Staples, I had never heard of Westport and all I had to check it out was a 1937 tour guide of New England. I looked up Westport and the entry read “A quaint fishing village and artists colony on Long Island Sound.” –Karl Decker
I think that the people that wrote these entries need a reality check or are maybe just very adolescent. It’s as though they never ventured out of Lower Fairfield County.
If it weren’t for F. Scott and Zelda spending one summer in Westport…..
And Lucy and Ricky moving to “The Country”…
They weren’t stuck up snobs
Before you freak out about what Urban Dictionary says about Westport, read what Urban Dictionary says about Urban Dictionary. Anyway, there’s nothing to worry about … according to Alexa, UrbanDictionary’s popularity rank in the US is 319 — in between RottenTomatoes.com and Xhamsterlivecams.com.
Maybe Westport needs to hire one of those reputation management companies. As a taxpayer, I would be happy to do that. I am sick of people thinking I’m a stuck up snob with overindulged kids.
All the perceptions promugated by the Urban Dictionary seem to be perpetuated by many of the residents of this town. While definitely not true, it seems to inflate some townfolk’s egos. Someone made a video called
“The Wonderful World of Westport” in the ’80’s and you would have thought this place was right next to nirvana on your check out lists. In truth, Westport is a great town with a majority of indiviuals with middle class values i.e hard working, love their kids and community. As to the drug scene, well perhaps I shall have to do some investigation?
Its all town in Fairfield County. Fairfield, Westport, Greenwich, Darien, New Canaan all get that same perception. Look up all those towns on UrbanDictionary, its uniform throughout.
Well, it’s TRUE about Darien and New Canaan
Well the car thing i have heard of however, I have never “recieved” ANY cars and I’m 29. I have never gotten “smashed” and I do not do drugs. I try to work my ass off and I still have no money, I am very happy with my Southern Connecticut state University BA degree thank you very much. Yeah Westport has a bad name, on the 1st day of classes here, we had an introduce yourself class. when I told the class I was from Westport, the professor said (and I quote) ” OH. . . OH my! Everyone stop! we have a Westporter in our class!” Its crazy what people think about westporters.
Congrats but weren’t a tiny bit flattered??
I mean all of fairfield county towns get that same treatment.
As a wise man once opined; Every stereotype has an emprical basis.