A "city" that is actually a town; northernmost Virginia but not NOVA; considered "South" by many. Residents love to hate it, though this is more of a popular movement than an individual decision. Big emphasis on apples - there used to be a lot of orchards and apple product production but many of those have now been sold and developed. However, apples still remain a defining feature of the town, as demonstrated by the town's largest public celebration every year, Apple Blossom, during which it is basically blasphemy to not be wearing pink and/or green.

Home to the one and only White House Apple Factory, as well as the legendary Snow White Grill (comparable to White Castle), the town usually shuts down pretty early (with stoplights starting to blink at 9 or 10 PM). Late night entertainment includes: bowling, WalMart, IHOP, strolls or burgers downtown or bars. Wide variety of characters, from the aloof county residents to the elite "old families" of the town.

Also a point of reference for surrounding, more rural areas and/or smaller towns such as Gore, Virginia, a popular place for camps and retreats with beautiful countryside and the birthplace of author Willa Cather.

Also affectionately known as: the Chester; Winkyville

*for the historically inclined, Winchester has been an important piece of many of our nation's formative battles and occurrences, especially in the Civil War era!
Harry: Who's that over there?
Lucy: That's the Smiths - they moved into that house on our street thirteen years ago!
Harry: Oh, so they're still new.

Rebecca: "I'm so excited to be going home to Winchester! There's nothing quite like the smell of fresh apple butter wafting through the air in the fall from the apple factory!"
(once she's home)
"Ugh I miss my friends and having a life."

John: Where are you from?
Alex: Frederick County.
John: Where?!
Alex: Winchester Virginia
John: Oooooh. Wait, where?
Alex: It's near Washington.
John: OK, so you're NOVA?
Alex: Nope not NOVA, northernmost Virginia.
by WINCchicky November 11, 2009
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A prestigious University which handled the deadliest single-gunman shootout in American history with poise and grace by uniting in a display of school spirit untouched by any other collegiate institution.
Anyone trying to exploit this site to make light of the loss of 32 invaluable lives at Virginia Tech needs to go rot in hell. It is disgusting that urbandictionary.com would approve some of the sickeningly vile definitions above.

HOKIES ARE NOT FORGOTTEN
by hokie4life July 3, 2007
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A great place to do things outdoors. When your here your surrounded by nice people unlike that piece of shit OHIO! All you people think is that people from West Virginia are dumb rednecks, well your wrong. West Virginia is without a doubt the best state in the fuckin country. So all you hatin sons a bitches can go suck a dick!!!!
West Virginia kicks ass!
by Forrest Loughry March 2, 2009
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A southern suburb of Washington, DC that is located in the rolling hills of northern Virginia. This community of "trust fund babies" and selfish, shallow "richers" will not allow economic growth or an actual working "blue collar" sect of people into it's town. Populated by rich coke heads that have old English style names such as "Chadwick Dunston Elffson Watley III", Middleburg is known for it's anti-gun, anti-religion, pro-abortion liberalism as well as it's talent to look down upon actual working people, because of all the "Old Money" floating around. "Fox Hunting", "Steeple Chase" as well as other wealthy English sports are the main attraction in this shallow place to live. If you don't have money, and your ancestors weren't Protestants from the Mayflower, don't bother going near this town. They'll chase you out with their Land-Rovers, Mercedes, and Cadillac Escalades.
If you're poor, don't bother visiting Middleburg, Virginia.
by Johnny Hates NOVA August 5, 2005
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The town that drains you of your will to live until you forget your previous life and become another close-minded and unbelievably idiotic resident of Southwest VA. The hills close you in. There is no escape.
newcomer: "did you hear in the news about the upheaval in Libya?"
resident of 2 yrs: "no, i don't care about stupid stuff like that in the outside world... i live in Wytheville Virginia!"
by thehillshaveeyes December 8, 2011
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where the real south begins a place where people don't try to hide there country accent and accept where they from and proud of it.
southern virginia the real south
by va kid May 14, 2007
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