I usually pray in a shul where they do not wear tefillin on Chol haMoed, however I do regularly wear them during this time, but pray at home so that I will not cause any undue strife. Thus, for the past couple of days I have been praying b'yehiduth in my sukkah.
This being said, tomorrow is Hoshana Rabbah and the Rav of my community has asked that everyone be in attendance. In addition, I am very close to the Rav and he particularly asked that I attend the minyan. My quandary is that on the one hand I want to be consistent and uphold the mitzvah of tefillin, but on the other hand I do not want to embarrass or disrespect the Rav of the community in any way. What should I do?
1. If you know the Rav of the community well, I would suggest you speak to him about this
matter and your difficulty with it. You might politely inquire if he is familiar with the numerous Hazalic sources which plainly indicate that tefillin are to be worn during Chol haMoed, and that wearing tefillin during Chol haMoed was the nearly universal practice of Am Yisrael until the advent of Sepher HaZoharin relatively recent times (as attested to by R. Yoseph Karo in his Keseph Mishne to Rambam’s MT Tefillin 4:10; see Hagahoth Maimoniyoth ad loc.).
2. I recommend not doing anything that will result in mahloket, even though you are 100% correct that tefillin should be worn during Chol haMoed.
3. If the Rav agrees to you wearing tefillin in shul during Chol haMoed (unlikely), then you have no problem. If not, I would suggest wearing the shel yad under your shirt/jacket etc. so that it is not visible, or wearing tefillin before or after going to shul. I would not recommend staying away from shul for this reason.
10th of Cheshvan, 5774 Wednesday, 13 October 2010