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There is a tradition that in the Messianic era,

Our Sages teach that when the Messiah arrives the festivals will cease to be observed, but Purim will continue to be observed. The Midrash (Mishlei 9) derives this unusual conclusion from a statement in Megillat Esther, (9:28) “the memory of Purim will never cease from among their descendants.”

from https://www.ou.org/holidays/purim/purim_is_forever/

This was brought up in discussions of Pesach in the future (in the third to last comment) and might be implicitly challenged by the future status of Tisha B'Av.

But in the Artscroll Machzor for Sukkot, the explanatory note on the Haftarah of the 1st day reads

this topic [Gog and Magog] is related to Succos because of the prophecy that those nations who would survive the wars would join Israel every year in celebrating the Succos festival.

(emphasis mine)

The prophecy is found later in that Haftarah.

How are we to understand the nature of holidays in the Messianic era if we have so many apparently contradictory positions about which holidays will and won't exist?

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  • Comments are not for extended discussion; this conversation has been moved to chat. Commented Oct 20, 2016 at 0:45
  • The commandments written in the Torah (which include all of the holidays) will never cease to be observed, even when Messiah comes, as it says in the Torah itself referring to its commands, "it shall be observed throughout all generations." [Note my usage of "shall" and not "will."] So based on this the holidays will always be observed. Period.
    – ezra
    Commented Oct 21, 2016 at 3:47

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