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4.
An absolutely shitty town and high school filled with terrible hippie liberals who sit around all day smoking (probably skipping practice) wishing they lived 40 minutes south with all the other "elite" Darien kids drinkin brain grenades. Don't live here or in Darien....ever.
Ryan Terrance Mcgrath!
by gaffer March 04, 2005
 
1.
One of the best towns in Connecticut, known for the academic excellence of their school system, and beautiful homes. Based on Mastery Test, and SAT scores, has the "smartest" school system in the state of Connecticut, and are ranked number 6 in the country, for the same statistic.
I live in Simsbury, possibly the best town in Connecticut, and it doesn't matter that my family pays so much in taxes because I have one of the best education systems in the country.
by Matt April 25, 2005
 
2.
A town in the state of Connecticut known by the elders as a very affluent area with a good education system and by the younger generation as a boring as fuck town. People from outside Simsbury think everybody is a douchbag from the town for several reasons including but not limited to: our general population being represented by stuck up douchbags who think they are the shit and drop the name Simsbury to try to equate themselves with wealth, many of us want you to think we are jackasses and spend our time fucking with you, the man at Dunkin Donuts was too stoned to properly toast their bagel, and all the worthwhile people die or move out. Still for some reason people come back to visit the town, probably because of memories of the crazy as fuck people you tend to find here from time to time and because you realize how much you liked the town after spending some time in NJ. One of the best things about Simsbury is that it is not Canton, our "ghetto/redneck" neighbors who are plagued by wannabe gansters and cracked out women. Granby, the northern neighbors, are known by many Simsbury residents for their Cumbys Chill Zones (slushies) and for the locals celebration of white power Wednesday. In Simsbury there is an obvious clash between the conservative old folk and the hippie youth.

Also if you live here you have a 99% chance of being white
well we are in Simsbury
by Royal-T-Slutts July 24, 2011
 
3.
a town filled with snobby kids who like to gossip, party, drink and smoke, they think they are better then everyone else, and the school system is the best around
where are you from?
simsbury!
oh you must be rich and stuck up
by laura janers February 26, 2011