1)

What was Moshe referring to when he said "Eleven days from Chorev"?

1.

Rashi: He was pointing to the damage that they had caused by sending the spies, 1 as a result of which they had to travel round Har Se'ir for forty years, 2 bearing in mind that Hashem was so keen to take them into Eretz Cana'an, that he curtailed the eleven days journey 3 from Har Chorev to Kadesh Barne'a, to three days. 4 But because they sinned, 5 they had to wander around Har Sinai for forty years.

2.

Ramban and Seforno (on Pasuk 19): The Torah is telling us that Hashem took Yisrael through the great and fearful desert because it was the shortest route from Chorev (Har Sinai) to Kadesh Barne'a (the outskirts of Har ha'Emori) 6 via Har Se'ir, and that they then wandered in the desert for forty years (due to their sins).

3.

Hadar Zekenim, Rosh and Targum Yonasan: Had they gone straight to Eretz Yisrael, it would have been a mere eleven-day journey. But due to their sins they delayed it, and had to go round Har Se'ir for 'many days'.


1

See Sifsei Chachamim DH 've'Ein Lehakshos'.

2

Seforno: Wandering aimlessly from place to place. In fact, Moshe pointed this out each time they encamped in one of those places - instead of going straight to Eretz Yisrael.

3

Seforno: Which He did by leading them through the desert, instead of taking them along the regular route via the land of Edom.

4

Rashi: From the twentieth of Iyar when they left Har Chorev, till the twenty-ninth of Sivan, when they sent the spies - minus the thirty days that they spent in Kivros ha'Ta'avah and the seven days that they waited for Miriam in Chatzeros (See also Rashbam, who disagrees with Rashi regarding some of the details).

5

Oznayim la'Torah: By desiring meat and complaining about the Manna. See Oznayim la'Torah, who pints out that they were otherwise poised to conquer Edom, Amon and Mo'av (the Kemi, Kenizi and Kadmoni) together with the seven nations of Cana'an.

6

Ramban: Which in turn, belonged to Yisrael.

2)

Here the Torah writes that it is an eleven-day journey from Chorev until Kadesh Barne'a (Midbar Paran, from where they sent the spies). But the Gemara in Shabbos (89a-b) equates Chorev and Midbar Paran?

1.

Moshav Zekenim (in Bamidbar 13:21): Chorev and Kadesh Barne'a are both in Midbar Sinai, which is one big desert, different parts of which have different names.

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