1878Education
Nettie George Speedy (1878–1957), journalist of Chicago Defender, founder of Chicago Women's Golf Club, the first woman to sit on the trustee board of Lane College, and the Pion...
1890Education
Kentucky Wesleyan College was located in the city from 1890 to 1954.
1899Military
Claude Sullivan, sports broadcaster
Allen Tate (1899–1979), poet associated with the Agrarians, a group of Southern poets, and most noted for "Ode to the Confederate Dead"
Helen...
1926History
== Economy ==
=== Small business ===
Ale-8-One, a Kentucky-specific brand of soft drink, has been bottled in Winchester since 1926.
1927Education
Preston Knowles, basketball player for the University of Louisville
Homer Ledford (1927–2006), instrument maker and bluegrass musician
Matt Long, TV's "Jack & Bobby", "Mad Men",...
1958History
Kentucky Route 1958 (Bypass Road) is an outer loop around the town.
1968Civil Rights
The last L&N passenger train was an unnamed Cincinnati - Atlanta remnant of the former Cincinnati - Jacksonville Flamingo; it was discontinued on March 7, 1968.
1972History
Fryer, psychiatrist whose speech in 1972 as "Dr.
1979Education
After Southeastern Christian College folded in 1979, the campus was preserved as a public park.
2000History
== Demographics ==
As of the census of 2000, there were 16,724 people, 6,907 households, and 4,620 families residing in the city.
2018Military
Army brigadier general
== In popular culture ==
A 2018 episode of The Dead Files was filmed in Winchester.