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1.
A prep school in Massachusetts which, although academically excellent, has suffered enormous bad press because of the actions of a few. The student body is incredibly intelligent and independent (albeit not very unified).
It has its share of normal teenage hormonal behavior, but, contrary to some news reports, is not home to extravagant orgies. Even the stereotypical stoners and shallow DSGs tend to be surprisingly intelligent. The administration occasionally feeds the students feel-good, politically correct crap. Boarders are very loyal to their dorms, and day students rally under the 'because our parents love us' slogan... such is life.
Nobles Kid: It'll be, like, really funny if we drive by Milton Academy and honk our horn, like, really loud at them!!! *guffaws*

Techie: *hiss* All your base are belong to us.

Freshman: *blinks*

DSG: Daddy's buying me these giant, fuzzy Uggs!

Speechie: *slinks off to rejoin his evil speechie clan*

Student Body: OHHHH SIXXX!! FOOOOORBES! YEAH HALLOWELL!! etc.
by i_am_sam89 January 02, 2006
 
2.
A Massachusetts prep school with an intelligent student body, despite they're inability to cross streets. "Milton" students are typically insane, but most will overlook this at first. Many celebrities, politicians, and other famous and wealthy people have graduated from this school.

However, Milton Academy is more known for that weird girl with the iPhone shuffling and screaming "SHELLY!" at the top of her lungs.
Milton Academy Student: So I was in AP Calculus when--

Aforementioned Girl: SHELLY!

MA Student: God, she's crazy.

Non-Milton Student: Maybe I don't want to go to this school...
by 98shiningstar February 22, 2012
 
3.
Prep school in Milton, MA.

None of the kids know how to cross streets. So, one should be careful when driving through. They tend to waltz into the road because in their classrooms, protected from the real world, they are taught that white stripes painted on the ground will protect them from speeding vehicles careening down a relatively main motorway.

Students are very sheltered within the confines of the classroom. They tend to: be ridiculous 'Lax Bros', get hit by cars, get lost, lack the understanding of how to really get by, and look down on public school kids in the town (referred to by such as 'townies').

However, students tend to be extraordinarily intelligent in the classroom despite being frightfully dim as regards the outside world. (e.g. lack of knowledge regarding public transit)
"Townie" 1: Need to sell the rest of this by Saturday
"Townie" 2: Let's find some Milton Academy kids, we'll get twice as--
THUNK!
"Townie" 1: Aw shit, I hit another one..

Milton Academy Kid 1: (looking at MBTA website on their Droid) So, Saturday night we can take the bus to Mattapan, then the redline to Downtown Crossing so we can get on the Orange Line to get to ChinaTown for some chinese food and Banksy! High-Five for knowledge!
Milton Academy Kid 2: Wait... The Buses go to the train stations?
by Milton02186 April 07, 2011