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1.
An annoying town that always cheats Winchester out of snowdays by being before them on the cancellations list and the first 6 letters being the same in both towns.
Look, a snow day! Winche!--ndon. Damn you, winchendon.
by bertherdenug April 03, 2006
 
2.
Lame ass town in north central Massachusetts filled with incest babies, white trash and dumb asses.
Look at that cross eyed mother fucker, he must be from Winchendon...
by PETE March 08, 2004
 
3.
a place in the middle of nowhere thats bigger than half the places in massahcusetts but has less people than a group of girls at a slumber party. the population is mostly female, and the guys that are around are really not that great, you're probably related to them anyways. the whole town is made up of pizza places and chinese food. and dunkins. the middle school and high school combined has a population of about 600. driving anywhere takes about a half an hour and you cant even get to anywhere good, besides Dennys, which is the best hangout at 2 in the am.
"hey i'm from winchendon"

"whats winchendon?"
by the cooler n-dawg October 12, 2007
 
4.
A black hole in North Central Massachusetts where hope goes to die. The only thing lower than the constituents average IQ is the property value. Surprisingly, the town of Winchendon also has a well known reputation of being the home of many incestuous relationships. The closest civilized outpost for the residents of the "winch" is the Pizzeria Uno in "Kmart Plaza" in the slightly less abhorrent Fitchburg Massachusetts. It takes approximately 40 minutes to get any relevant from the Winch, and it is about 90 minutes from Boston. If you like sadness, dumb, driving long distances, lousy restaurants, being associated with incest, and camouflage hunting vests, then you would like the Winch.
I'm from Winchendon

Congratulations, you stupid Asshole!
by SweaterVestRandy April 19, 2011
 
5.
A town where, by having sexual intercourse with one person, you are forever sexually linked to every other town member of a certain age bracket, given the past sexual conquests of your partner.
"oh, winchendon, eh? the dirty winch."
by walgreen79 October 14, 2008