In the article What Are The Signs of the Last Days, we are reminded that Jesus cautions us to pray that our flight be not in winter (Mark 13:18) (Making your escape perilous or tempting you to delay your flight. Matthew 24:20 adds “or on the sabbath day.”)
Why should we pray that our flight not be in winter?
Here is a variety of Bible commentaries. “When days are short, roads bad, the weather inclement; and when to lodge in mountains, is very incommodious, and uncomfortable.” (John Gill’s Exposition of the Bible) “Such is the vanity of the creature, which the time may often be, when the greatest comforts may prove the greatest burdens. It would likewise be very uncomfortable, if they should be forced to flee in the winter (v. 18), when the weather and ways were bad, when the roads would be scarcely passable, especially in
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the mountains to which they must flee. If there be no remedy but that trouble must come, yet we may desire and pray that, if it be God’s will, the circumstances of it may be so ordered as to be a mitigation of the trouble; and when things are bad, we ought to consider they might have been worse.
It is bad to be forced to flee, but it would have been worse if it had been in the winter.” (Matthew Henry Commentary) “Not in the winter. Because the streams were then impassable torrents from the heavy rains and the weather cold and wet, hard on homeless people. Nor on the sabbath. Because then the gates of the city were closed, preventing departure. History tells us that the army of Cestius Gallus enclosed Jerusalem in A. D. 67, then deterred by its strength, retired to Cæsarea. This was the signal for which the church waited, and it then fled beyond the Jordan. The sign given by the Lord for the flight, the environment of the city by the Romans, and the panic that caused their sudden withdrawal, occurred on Tuesday, in October. Hence the flight was neither in the winter, nor on the Sabbath day.” (People’s New Testament)
People’s New Testament tells us what actually did happen when the Roman Armies returned. “The account given by Josephus, the Jewish historian who witnessed and recorded the war, is almost an echo of the predictions of Christ. Women ate their own children from starvation; the Jews within the city fought each other as well as the Roman army; on August 10, A. D. 70, ) the city was stormed and there was a universal massacre; 1,100,00 persons perished, and 100,000 survivors were sold into slavery.” (see the 1st century on the Biblical Timeline Prior to the second coming of Christ similar events will occur as discussed in the Signs of the Times article on this site.