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2.
Osterville is one of the preppiest places in MA. There are two different country clubs, Oyster Harbors and Wianno Club. Most of the people that belong there are stuck up. All the cool people beach it at Dowses. Dowses is where the notorious "Fab Five" hang out and theyr'e up to no good. Also, The Wianno Yacht Club is the shit. They have dances every summer that kick-ass. A normal night at Cape Cod may include getting wasted at the Foxhole/ Joe's Twin Villa and then going skinny dipping at the beach and then drinking some more. Most people that live in Osterville have one or more boats and can usually be found wearing Polo, Lily Pulitzer, Abercrombie etc. There are very few races other than white that live in Osterville. There are two groups of kids in Osterville. The townies and the kids that come down in the summer. The townies usually hate Cape Cod in the winter because its boring but then in the summer they hate it because the summer kids annoy them. Personally, I have had bad experiences with townies (*COUGH T *COUGH ess). There is usually no reason to ever leave Osterville in the summer. It has everything you need beaches, resturaunts, grocery stores, library. Osterville probably has about one fucking million real estate offices because they make so mcuh money selling mansions.
Local 1: Hey look at that kid wearing Roca Wear.
Local 2: He must be from Hyannis or something.
Local 1: Yeah, he's definetly not from Osterville.

Tourist 1: Woah we haven't driven for more than half a mile and we've already passed 23 real estate offices.
Tourist 2: Oh, we must be in Osterville.

Local 1: Who are those obnoxious kids sitting on the bench?
Local 2: Oh, I've heard of them they must be the "Fab Five".

Local 1: Who's that girl on the street corner giving away free cupcakes?
Local 2: It must be that girl T***.
by Summa summa summa time June 18, 2005
 
1.
A nice little quaint village in the winter where all the locals go to either CCA, Barnstable High or some New England boarding school. Then the rich summer people come, along with the tourists, and the booze and the various illegal substances, to go bridge-jumping, midnight tubing, driving on various things that move, PARTYING in expensive preppy mansions (or locals homes) and/or doing anything while under the infleunce. (This is everyone who lives on Seaview, or has a dock.) The tourists demand to know if there is a beach on the Cape-when they are two steps away from the beach's parking lot- and where lime-green suits around town-perfectly acceptable when your sleeping...by yourself... Then there the nice summer people that can be your bestest friends!
Example 1:
C (on Vespa): Party at A's house! Beer Pong Championships!
L (in Porsche): I'm so there!

Example 2:
Local 1 (at Golf Club): You see Mr. Fancypants of Oyster Harbors over there?
Local 2: Yeah!
Local 1: Well, lets go and play some games with him!
(Both Locals go and hid in the bushes)
(Mr. Fancypants prepares to swing)
(At the same time Local 1 takes foghorn and presses the button)

Example 3:
Richy 1: I belong to all the fancy clubs in town, Wianno, Hyannis Port and Oyster Harbors.
Local to Richy 1: (Slap)

Example 4:
Nice Summer Person: Do u want to go to Sweet Tomatoes, for pizza and rootbeer?
Local 1: Finally, a nice, normal, sober summer person!
by anon... April 28, 2005
 
3.
...beers on the beach...golfing barefoot on somebody elses dollar...driving somebody elses new convertible...crashing in somebody elses oceanfront mansion...bridge jumping...rope swinging...living in board shorts...eating like a king...drinking like a fish...living like you're dying...Ostervillin' through life...thanks to y'all for being such sweet hosts...see you soon!
examples have been forgone to protect the guilty...
by Lynchie April 15, 2005
 
4.
Osterville, MA. is the place to be from memorial day till labor day people will drive for an entire day from Fl or MI just to spend a week, there are no cops on land the only person to bust u for anything is the habor master. Pretty much every one there is an English Yankee. The people that belong to the Wianno club are stuck up and if u wanna have fun u gotta hang out with the yatch club kids.
Honey do u rember john smiths house number there are five people with his name on the same street in this Osterville, MA phone book
by yatch club goer August 30, 2005
 
5.
a village in cape cod.

one of the wealthiest and most beautiful villages in massachusetts.

most known as a summer vacation spot. a quaint beach town with pleasant preppy reisdents, country clubs, Rolls Royces, and beautiful sailboats.
Osterville, Ma. The pride and joy of Cape Cod.

Reisdents of Osterville, Ma are "Blissfully unaware"
by capecodlover March 31, 2005