Depends on what source you believe. ...
"more than
seventy times"
http://www.encyclopediavirginia.org/Winchester_During_the_Civil_War
"as many as
72 times"
"changing hands
dozens of times"
http://www.civilwar.org/battlefield...ester-history-articles/winchesteradelman.html
military control of the town switched hands
nearly 100 times, though a recent tally of formal changes of possession sets the number at
14.
http://www.historynet.com/wincheste...g-americas-civil-war.htm#sthash.C2hWNXu1.dpuf
The town of Winchester, Virginia changed hands
over 70 times during the Civil War.
http://www.omgfacts.com/lists/5560/...hands-over-70-times-during-the-Civil-War-abf5
In her book "Defend the Valley: A Shenandoah Family in the Civil War," Margaretta Barton Colt
included a list of times the town was occupied.
It denoted
13 occupations, the shortest being Union troops' July 21-24, 1864, stay that ended when
Jubal Early drove them through Winchester during the Second Battle of Kernstown.
That's the figure preferred by Joe Whitehorne, a former Army staff historian who taught at Lord
Fairfax Community College for 21 years and a contributor to numerous books, including some on
the Civil War.
http://www.shenandoahatwar.org/News-Press/How-Many-Times-Did-Winchester-Change-Hands
position taken by local historian Ben Ritter, who said he considers
72 to be the number
of times Winchester changed hands during the war.
http://www.shenandoahatwar.org/News-Press/How-Many-Times-Did-Winchester-Change-Hands
While a considerable gap is evident between Colt's representation of 13 occupations of Winchester
and Chase's chronicle of 72 control shifts, some accounts provide a greater number.
The online archives of The New York Times contain a list of federal and Confederate occupations
that the newspaper published on Sept. 17, 1865, under the headline "A Town Well Occupied:
Three years' Experience of Winchester, Va."
Union troops occupied the town 48 times, it stated, and Confederates controlled it 27 times. It was
occupied by both sides in one day during a battle, making a
final total of 76 occupations.
http://www.shenandoahatwar.org/News-Press/How-Many-Times-Did-Winchester-Change-Hands
The diaries of Chase and Kate Sperry were used in creating the list, but Mary Greenhow Lee's
diary was his primary source. Delauter said he thinks more than one source is needed "to see what
really happened."
He highlighted events that accounted for a changing of hands and came up with
96 times (though
97 are marked with an asterisk denoting such an occurrence) even as he said the true number
might
exceed 100.
http://www.shenandoahatwar.org/News-Press/How-Many-Times-Did-Winchester-Change-Hands
I've spent over an hour and a half reading resources to answer this question and have come up with multiple answers
anywhere from 13 to over 100 times.