On New Year's Eve 1862, the citizens of Winchester were preparing for occupation by Union General and abolitionist Robert Milroy. The first day of 1863 was to be the date that Abraham Lincoln's Emancipation Proclamation was set to take effect. It was expected that the announcement was to be made at the courthouse and the bells rung. Three of Winchester's female diarists recorded their thoughts that evening and on New Years Day.
Confederate supporter Laura Lee wrote on December 31, 1862,
"New Year's Eve. A sad and dismal time, weather dark and gloomy, and everyone more depressed than I have ever seen them. We are told that tomorrow emancipation is to be proclaimed from the Courthouse, with the ringing of bells, and that the soldiers are to be quartered on the citizens without distinction. They do not have wood from the country, but tear down the few fences that were left, and the outhouses and wooden buildings around the town. They have torn the [Winchester] Academy to pieces, and are now destroying the Market House. There seems to be no hope of relief from our dismay."
Mary Greenhow Lee was perhaps the town's most devoted Confederate woman. She wrote that evening,
"The excitment of this morning was caused by the Yankees firing at a mark; if the rumors of the day are correct, Milroy with his force is to be here to-night or to-morrow, it is said. They are to be quartered in the private houses...I believe the threat will be carried out & though the may not infest every house, no one can tell who will escape...It is said that bells are to be rung to-morrow, & the emancipation of the slaves, to be publicly announced. Each day brings new threats of atrocities."
Union supporter Julia Chase wrote on January 1st,
"Clear but cold today. Some prisoners brought in this morning. Father is still at Baltimore, we hope to see him soon. According to the President's Proclamation, all the slaves are to be freed from today. This will give great dissatisfaction to slaveholders but joy to the Negroes. I doubt whether they will be better off by their freedom."