Albert Barnes Commentary Matthew 24:20

"And pray ye that your flight be not in the winter, neither on a sabbath:" — Matthew 24:20 (ASV)

But pray you, etc. The destruction was certainly coming. It could not be prevented. Yet it was right to pray for a mitigation of the circumstances, that it might be as mild as possible. So we know that calamity is before us; sickness, pain, bereavement, and death are in our path. Yet though we know that these things must come upon us, it is right to pray that they may come in as mild a manner as may be consistent with the will of God. We must die; but it is right to pray that the pains of our dying may be neither long nor severe.

In the winter. On account of the cold, storms, and so on. To be turned from home then, and compelled to take up their abode in caverns, would be a double calamity.

Neither on the Sabbath day. Journeys were prohibited by the law on the Sabbath, Exodus 16:29. The law of Moses did not mention the distance to which persons might go on the Sabbath; but most of the Jews maintained that it should not be more than two thousand cubits. Some supposed that it was seven furlongs, or nearly a mile. This distance was allowed so that they might go to their places of worship.

Most of them held that it was not lawful to go farther, under any circumstances of war or affliction. Jesus teaches them to pray that their flight might not be on the Sabbath, because if they should not go farther than a Sabbath day's journey, they would not be beyond the reach of danger; and if they did, they would be exposed to the charge of violating the law.

It should be added that it was almost impracticable to travel in Judea on that day, as the gates of the cities were usually closed, Nehemiah 13:19–22.