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1.
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
44 14
 
2.
an old quaint southern town in northwestern virginia, the shenandoah valley...they are very proud of this parade called appleblossom which is pretty much the one time when it doesn't feel like a ghost town...the highschool looks like a university...the university looks like a middle school...it's a strong recovery town, lots of aa meetings, and rehab/recovery programs such as New Lifestyles, Edgehill, and ...some other big detox hospital i can't remember the name of...home to celebrities such as Stephen Bossidy (living) and Patsy Cline (dead)
and they have two walmart supercenters...and a street called walmart drive...it's pretty much the only place you see people actually walking around.
me: i got sent away to this rehab program.
friend: where?
me: winchester virginia.
friend: oh...um..where the fuck is that?
me: middle of nowhere
friend: is it nice?
me: if you're into walmart, ghost towns, and aa, then yeah, awesome.
by rjul May 09, 2009
31 35