What is the significance of the fact that the Cloud rose from the Mishkan ha'Eidus on the twentieth of Iyar?
Rashi #1: It teaches us that they encamped in front of Har Sinai ten days short of a year. 1
Rashi #2: In Devarim: It teaches us that they traveled from Chorev to Kadesh Barne'a (the last stop before entering Eretz Cana'an) 2 in three days - instead of the eleven days that it would normally have taken. 3
Seforno: It teaches us that no sooner were the trumpets made - immediately following the Korban Pesach Sheini, than they were used to announce Yisrael's departure from Har Sinai.
Oznayim la'Torsh (according to Kabalah: Because the Cloud did not rise from the Camp as long as the Simchah of Pesach was present - and the Crown (the Simchah) of Pesach remained thirty days after Pesach. 4
Rashi: They arrived at Har Sinai on Rosh Chodesh Sivan and left on the twentieth of Iyar of the following year.
According to the Seforno, it was actually in Eretz Cana'an.
Refer to Devarim 1:2:1:1****.
See Ozayam la'Torah.
When the Cloud rose from the Mishkan ha'Eidus, where was it about to lead them?
Rashi and Seforno: It was about to lead them to Kadeish Barne'a 1 (the first town that they would encounter on the border of Eretz Cana'an - Seforno) from where they were destined to enter Eretz Yisrael and begin the conquest of Cana'an. 2
A journey that should have taken eleven days, but which took them only three (See Rashi in Devarim, 1:2)..
Seforno: See Devarim, 1:19, and Rashi there on Pasuk 29.


