In Hebrew the phrase (Deut. 16:16) is shalosh p’amim bashanah. Shalosh can be spelt with a vav but it does not need to be. In this verse the vav is there. Some say that since the numerical value of vav is six, there is a secondary meaning – that six times a year a person should visit their teacher, on Pesach, Shavu’ot and Sukkot, on Rosh HaShanah, Yom Kippur and Sh’mini Atzeret.
The question is why one should visit a teacher at all and why on these particular occasions, with a further question: what happens if the teacher is no longer alive.
Visiting a teacher is a way of showing respect. It reconstructs the days when the teacher’s personality and influence surrounded all one thought and did. It renews the ideas and interpretations that came from the sage. If the teacher has passed away a “visit” involves looking at their writings or at least trying to re-evoke the lessons and conversations that may have taken place years before.
Why on these particular days? Not only because they are the major days in the year but because each one signifies a principle that every student needs – aspirations (Rosh HaShanah), overcoming mistakes (Yom Kippur), being yourself (Pesach), a moral compass (Shavu’ot), the need for Divine protection (Sukkot) and never letting the teaching fade (Sh’mini Atzeret).
Which teacher should one visit, either physically or notionally? The one who was your greatest mentor.
In my own case I had the blessing to revisit my mentor’s home years after I left his classroom. It was a joy in both the personal and the intellectual-spiritual sense. It also taught me humility. By then I was an adult and a teacher myself, and it was good to be reminded how much more I still had to learn.