Me'ein Shalosh on Grapes from Mitzpeh Ramon

Answer

[1]The Gemara (Berachot 44a) distinguishes between fruits of the Land of Israel, over which one recites al haeitz ve'al peiroteha, and fruits from outside the Land of Israel, over which one recites al haeitz ve'al hapeirot. This is stated explicitly in the Gemara:

Rabba bar Mari said in the name of Rabbi Yehoshua ben Levi: Anything that is from the seven species for which the Land of Israel was praised, at the start, one recites over it: Who creates fruit of the tree, and afterward and at the end, one blessing abridged from the three … Rav Chisda said: For the land and for its fruits. Rabbi Yocḥanan said: For the land and for the fruits. Rav Amram said: They do not disagree; rather, this blessing, for its fruits, is for us, in Babylonia, and this blessing, for the fruits, is for them, in the Land of Israel. Rav Nacḥman bar Yitzcḥak strongly objects: They, in the Land of Israel, eat and we, in Babylonia, recite a blessing? (How can we, residents of Babylonia, recite a blessing for the fruits of the Land of Israel while eating the fruits of Babylonia?) Rather, reverse the opinions: Rav Chisda said: For the land and for the fruits (al ha'aretz ve'al hapeirot), and Rabbi Yoḥanan said: For the land and for its fruits (al ha'aretz ve'al peiroteha).

When reciting al ha'aretz ve'al peirioteha, one acknowledges the connection between the fruits and the place of their growth. Doing so emphasizes that in the Land of Israel, the fruits draw holiness from the land, as stated by the Bach (OC 208): 'The lofty holiness of the land is also imparted to its fruits, which draw from the holiness of the Divine Presence residing within the land." This sentiment is echoed by the students of Rabbeinu Yonah, who explained that the custom in the Land of Israel is a form of praise for the land:

And they do not disagree; this refers to us while that refers to them. That is to say, we, who do not live in the Land of Israel, should say al ha'aretz ve'al hapeirot. However, sons of the Land of Israel, since they live in the Land of Israel and in light of the praise for the land, they should explicitly mention the fruits of the land and say al ha'aretz ve'al peiroteha.

The question, then, stems from the status of Mitzpeh Ramon: is it considered part of the Land of Israel for all intents and purposes, or not? The Chida on Birkei Yosef (OC 208:11) discusses whether one should recite al ha'aretz ve'al peirioteha over fruits that grew in an area included within the olei Mitzrayim boundaries but not olei Bavel. He also addresses the question of the blessing formula for fruits from outside the Land of Israel brought into the land, noting a dispute among the posekim. Some later halachic authorities have cited the Chida, mixed up the questions, and erroneously concluded that the Chida's conclusion was that one should say "al ha'aretz ve'al hapeirot."

Rabbi Moshe Shternbuch, in Teshuvot Vehanhagot also discusses the issue of saying peiroteha vs. al hapeirot on fruit from olei Mitzrayim, noting that the answer hinges on the fundamental distinction between the fruits of the Land of Israel and those from outside the Land of Israel: is it the uplifted quality of the Land of Israel (also present in the olei Mitzrayim territory)or the sanctity of the Land of Israel vis-à-vis the obligation of mitzvot dependent on the Land of Israel (which does not apply in olei Mitzrayim territory).?

In my humble opinion, based on the words of Rabbeinu Yonah (ibid.) and other Rishonim, it seems that the defining issue is the uplifted virtue of the Land of Israel, which is why they mentioned the praise of the Land, not its sanctity regarding the land-dependent mitzvot. The Kaftor Vaferach notes this, and is cited by Rabbi A.Y. Kook in his introduction Shabbat Ha'aretz (15), that there are two aspects of the Land of Israel: the land in terms of the obligations of the land-dependent mitzvot and the land in terms of its lofty status and sanctity, which do not depend on being conquered or settled, rather on G-d's promise to Avraham Avinu (i.e. gevulot hahavtachah).

In light of the above, one should say on the fruit growing in the olei Mitzrayim territories al ha'aretz ve'al peiroteha. Likewise, the Chida on Birkei Yosef stated: "And it seems to me that if the fruit from the first conquest, even though the land is not currently sacred, it is still proper to recite the blessing over its fruits."

With regard to Mitzpeh Ramon, Rabbi Yaakov Ariel addressed the status of separating challah there that it is certainly not within the olei Bavel borders and that there is a doubt whether it is even within the olei Mitzrayim borders. Perhaps it is even part of the conquest of Shlomo Hamelech. In any case, it certainly is not outside the Land of Israel, since it is part of gevulot hahavtachah. If so, the place certainly has the lofty status of the Land of Israel; it follows that one should say on the fruits growing there al ha'aretz ve'al peiroteha.

Conclusion

One should conclude me'ein shalosh with al peiroteha in the olei Mitzrayim areas, Mitzpeh Ramon included. This also holds true throughout gevulot hahavtachah.