05/26/2026
Just this week, 3 people have asked about the origin of Windy Hollow. Truth is, I don't really know! But maybe someone does. It probably isn't because it is in a hollow....well, you wouldn't think that if you ever rode your bike up Ditney (according to Dad and others or Dithey according to maps, also locally known as Rafferty's) Hill! But i was able to do a bit of research on it and found these articles from the Owensboro newspapers.
early!
Windy Hollow May 1878
Part 1 –
I often get questioned on how the Windy Hollow area got its name and the truth is, I don’t know. So, I have been doing a tad bit of research and found a mention of Windy Hollow in the “Owensboro Messenger” in 1878. Articles that follow over the next 3 weeks are fascinating and almost seem fictional. I will share 3 stories where I have found the very first mentions of Windy Hollow over the next few Mondays as my .
May 8, 1878 – “Owensboro Messenger”, Owensboro, KY
Headline on page 3:
“THE PRIMARY ELECTION WAR IN VANOVER PRECINCT”, secondary headline: “The Charges, Captures, Recaptures and Retreats”
“The primary election was held at the Dragston school house, at the west end of the lane between Samuel Moseley and Dragston’s, on the new cut road, known as the Slip up and Blue Ruin Road.”
So – I have no idea where Draston’s school house was located and have never heard of Slip up and Blue Ruin Road!! Maybe someone can help map those locations! It could be possible that the Samuel Mosely family is where Moseleyville got its name although his may have been spelled differently, or an “e” was later added or the paper spelled it incorrectly in the article. I’m not sure!
Back to the article: “The officers of the election were as follows: Wm. Short and Samuel Mosely, judges: Wm. Clark, sheriff; G. W. Oglesby, clerk. At the proper hour they opened the polls and voting commenced. Every thing went off quietly with the exception of a small skirmish or two ; though all of the forces held their ground until about 10 o’clock, A. M. Then the first shot was fired, and the clash came by a brilliant charge from the right wing, made by the first windy hollow battalion, commanded by W. C. Vanover. They succeeded in capturing the polls, though not much damage was done in the charge, some few fallen and six wounded. The officers of the election retreated in good order, and being reinforced made a gallant charge, commanded by Colonel Short, drove back the enemy and succeeded in recapturing the polls without any loss.”
So, this is the first mention of Windy Hollow but doesn’t help on exactly where that may be but there is more to follow!!
“Voting went on in regular order with the exception of a little skirmishing on the front lines until about 3 o'clock, P.M., when the third charge was made by the German cavalry, commanded by General Wm. Cohan, who succeeded in capturing and destroying the poll books. The officers again retreated in bad order, but being once more rallied by their brave commander, Colonel Short, made one more brilliant charge and succeeded in recapturing the remaining fragments of the poll books, which they held until the last. General Cohan being defeated, retreated in good order. Colonel Short being victorious over the bloody field, came to the front and delivered a Democratic speech. The crowd dispersed and went home, except those who registered at Green Wood’s Tavern.”
Anyone else think this is craziness and could be the start of an awesome fiction book!!!
To wrap up this first newspaper report, let’s continue! “It is stated that the Vanover’s Precinct has declared her independence, that she intends to erect a capital of her own. The situation is not yet decided upon. It will be Blue Ruin or Slipup. All being quiet at present, and the train being ready, I am compelled to close. Fast Time.” Another assumption is Fast Time is the writer.
In all the conversations with Dad, a lifelong resident/landowner in Windy Hollow, I can’t recall him ever mentioning Blue Ruin or Slipup. Dad’s family moved to the area in the 1920’s, just 40-50 years after this saga but he never shared any info he may have heard.
Join us next week as we get the second article and a little more information about the skirmish and another mention of Windy Hollow.
