Midras Yehezkiel 41:7: Sifrei Devarim, Shir HaShirim Rabbah, Midrash Tanchuma Buber & Midrash Tanchuma

Similarly, R. Yehudah expounded (Zechariah 9:1) "A burden (of prophecy) in the land of chadrach and Damascus is its resting place.": This ("chadrach") refers to the Messiah who will be "chad" ("sharp") to the Canaanites, and "rach" ("soft") to Israel" — whereupon R. Yossi b. Dormaskith said to him: Yehudah berebbi, why do you distort the verses for us? I testify by heaven and earth that I am from Damascus and there is a place called Chadrach there. And how do I understand "and Damascus is (its) resting place"? (As meaning) that Jerusalem is destined to extend until Damascus; "(its) resting place" is Jerusalem, as it is written (Psalms 132:19) "This (Jerusalem) is My resting place forever." R. Yehudah: How do you understand (Jeremiah 30:18) "And the city will be built on its foundation"? R. Yossi: (As meaning) that (though) Jerusalem is not destined to move from its place (i.e., from its foundation), it will expand from its sides). How do I understand (Ezekiel 91:7) "And there was an enlarging and a winding about upwards, etc."? Eretz Yisrael is destined to broaden and rise from all of her sides like a fig, which is narrow below and broad above, and the gates of Jerusalem are destined to reach until Damascus. And thus is it written (Song of Songs 7:5) "Your nose is like the tower of Levanon, which looks towards Damascus." And the exiles will come and rest therein, as it is written "and Damascus is His resting place," and (Isaiah 2:2-3) "And it will be in the end of days the mountain of the L-rd's house will be established in the top of the mountains and will be exalted above the hills, and all the nations will flow unto it. And many peoples will go and say: Come, let us go up to the house of the L-rd, to the house of the G-d of Jacob, and He will teach us of His ways and we will walk in His paths. For from Zion will go forth Torah, and the words of the L-rd from Jerusalem."

“Your nose is like the tower of Lebanon,” just as the nose is located at the highest part of a person, so the Temple is located at the highest part of the world. Just as the nose has much jewelry suspended from it,³⁴Although people generally do not suspend much jewelry from their nose, it was customary to include one’s most beautiful jewel in a nose ring (Yefei Kol). Alternatively, the term nose [af] in this instance includes the area up to the forehead, from which people would suspend various types of chains and jewelry (Matnot Kehuna). so do priesthood, Levitical status, and kingship descend from Jacob. “Like the tower of Lebanon,”³⁵Many commentaries (see, e.g., Matnot Kehuna) assert that the text should read: “Like the tower of Lebanon,” this is the Temple, as it is stated… as it is stated: “This good mountain and the Lebanon” (Deuteronomy 3:25). Rabbi Tavyomi said: Because it whitens [malbin] the iniquities of Israel like snow, as it is stated: “If your sins will be like scarlet they will become white as snow” (Isaiah 1:18). Rabbi Shimon ben Yoḥai says: Because all the hearts [levavot] rejoice there, as it is stated: “Beautiful in its view, joy of all the land” (Psalms 48:3). The Rabbis say: [It is so called] because of [what is stated]: “My eyes and My heart [libi] will be there for all days” (I Kings 9:3).
“Overlooking Damascus,” Rabbi Yoḥanan said: Jerusalem is destined to reach until the gates of Damascus, as it is stated: “A prophecy, the word of the Lord: Ḥadrakh [and Damascus]” (Zechariah 9:1). What is Ḥadrakh? Rabbi Yehuda and Rabbi Neḥamya, Rabbi Yehuda said: There is a place that is called Ḥadrakh. Rabbi Yosei ben Durmaskit said to him: By the Temple service, I am from Damascus and there is a place there named Ḥadrakh. Rabbi Neḥemya said: This is the messianic king who is sharp [ḥad] and gentle [rakh]; sharp to the nations and gentle to Israel.
Another matter, Ḥadrakh, this is the messianic king who is destined to guide [lehadrikh] all mankind in repentance before the Holy One blessed be He. “Damascus is His resting place” (Zechariah 9:1). Is Damascus His resting place? But is His resting place not the Temple, as it is stated: “This is My resting place forever” (Psalms 132:14)? He said to him: Jerusalem is destined to expand on all its sides until it reaches the gates of Damascus, and all the exiles will come and rest under its auspices, to realize what is stated: “Damascus is His resting place,” His resting place will reach Damascus.
How does Rabbi Yoḥanan realize: “The city will be rebuilt on its mound” (Jeremiah 30:18)?³⁶This verse implies that it will be rebuilt upon its original location, but will not expand significantly beyond its original location. Like a fig tree that is narrow below and wide above, so Jerusalem is destined to expand on all its sides, and all the exiles will come and rest under its auspices, to realize what is stated: “For you will spread right and left” (Isaiah 54:3). This is lengthwise; from where is it derived [that it will expand] widthwise? The verse states: “From the Tower of Ḥananel to the winepresses of the king” (Zechariah 14:10). Rabbi Zakkai the Great said: Until the pits of Rifa,³⁷Some assert that the correct reading is “the pits of Jaffa” (see Etz Yosef). In any event, the reference is to a location on the Mediterranean coastline in the land of Israel. until the winepresses that the King of kings, the Holy One blessed be He, dug out;³⁸This is a reference to the oceans. that is lengthwise and widthwise. From where is upward [that it will expand] derived? The verse states: “The side-chambers widened and wound about higher and higher” (Ezekiel 41:7). It is taught: Jerusalem is destined to expand and ascend and reach the Throne of Glory, until you will say: “The place is crowded for me” (Isaiah 49:20).³⁹Even when Jerusalem expands so greatly in all directions, it will still be crowded due to all the exiles who will return there. Rabbi Yosei ben Rabbi Yirmeya said: We have still not learned the praise of Jerusalem. From where do you learn its praise? From its walls, as it is stated: “I will be for it, the utterance of the Lord, a wall of fire all around” (Zechariah 2:9).

Another interpretation (of Cant. 3:11): ON HIS WEDDING DAY, on Sinai.³⁶Cf. Cant. R. 5:11:2; PRK 26:9. (Ibid., cont.:) ON THE DAY OF HIS JOYFUL HEART, in Jerusalem. David said (in Ps. 48:3 [2]): BEAUTEOUS LANDSCAPE, THE JOY OF THE WHOLE EARTH, <EVEN MOUNT ZION>….³⁷See Cant. R. 7:5:3. <It is> like a fig in that it is narrow below and wide above, like what is stated (in Ezek. 41:7): AND IT BECAME WIDER AS IT WOUND ABOUT HIGHER AND HIGHER….