623. ʿĀʾishah (may Allah be pleased with her) reported: “When the Prophet ﷺ came to Mecca, he entered it from its upper side and left from its lower side.” Agreed upon (1).

Vocabulary
• Upper side: the pass of al-Ḥajūn (ḥāʾ with fatḥa), also called Kadāʾ (kāf with fatḥa and a final long alif). It is the road that runs between the two cemeteries of al-Maʿlā.
• Lower side: the pass of Kudā (kāf with ḍamma and a final short alif, like Hudā). It is now known as Riʿ al-Rassām, the road that comes from Ḥārat al-Bāb toward Jarwal by the Dome of Maḥmūd. A thaniyyah is any path that lies between two mountains.

Lessons derived from the ḥadīth

1. In this report the Prophet ﷺ entered Mecca by its upper pass. That was the route he used when he conquered the city in Ramadan of year eight AH, as also stated by ʿĀʾishah.
2. One wording of Ibn ʿUmar’s narration in the two Ṣaḥīḥs says: “The Messenger of Allah ﷺ would enter by the upper pass and leave by the lower pass,” indicating that these were his regular entry and exit routes whether he came as a commander, a pilgrim, or an ʿumrah-performer. Whoever can do so is therefore recommended to follow this practice.
3. Ibn Ḥajar writes in Fatḥ al-Bārī that scholars differed over why the Prophet ﷺ chose different roads. Some said it was so every group along each path could be blessed by him; others said ascending at entry suited the veneration of the place and descending at departure signalled farewell; others maintained that Abraham (as) had entered from that side; still others noted that those coming from that direction approach while facing the Kaʿbah.

I say: It may simply be that this entrance and exit were the easiest for him when arriving and departing—Allah knows best.