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You understand, I think, why there was a doubt about the day of Rosh Hashana and they needed two days (on the day after 29 Elul no one knew if witnesses would come or not, etc.). Thus, in fact, every date (eg.) on the Hebrew calendar had a one-day doubt to it (if you lived far enough away that messengers couldn't get to you in that number of days), either ...


Here's a piece on Chabad.org explaining it. Basically, it is on Elul 30 and Tishrei 1 -- the only problem is that Elul was set to only have 29 days. Back in the days of witness-based Rosh Chodesh, Elul sometimes had 29 and sometimes had 30 days. If it ended up having 29, then the day after (Tishrei 1) would be Rosh Hashanah and Tishrei 2 would be an ...

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