On Jewish holidays (such as Yom Tovim for Sukkot, Shminei Atzeret, Simchat Torah and Shavuot), Gray Academy is closed.
 
In his sermon on Yom Kippur, and in a conversation I have had with him since, Rabbi Green pointed out that although the school is closed for these holidays, it's not as if most of the kids are coming to synagogue on those days. Rabbi Green is correct. For most children, whose parents are not observant and in fact are working that day, these holidays don't enforce their Jewish identity at all--they become "free" days where they end up going to the mall with their friends, etc.
 
I would have thought that on those days we'd be better served as a community if on Jewish holidays (aside from Rosh Hashanah, Yom Kippur, and the first two Yom Tovim of Passover) Gray academy was open and arranged to have the children be bused to synagogues to participate in services, or in junior congregation and holiday programming for younger children. Of course, those parents who are observant wouldn't have to send their children to school at all--they would go to synagogue with their families etc. But, parents who were going to work anyways on those days (as most are), could drop their children off as per usual to school and then the school would take them to services (where they would participate--potentially they could even be asked to lead part of the services) and have a special lunch afterward back at the school, an extended recess and an afternoon discussion about an aspect of the holiday, etc. There would not need to be regular learning on those days, no writing or note taking, etc. 
 
However, this would mean that there would have to be a skeleton staff at the school operating to take the children to synagogue, lead the discussion after services, etc.  The main stumbling block to enacting this idea from what I understand is that under the teachers' unionized contract at Gray Academy it is enshrined that these holidays are not to be work days, such that Gray Academy will always be closed. (Teachers are never likely to agree to change this aspect of their contract).
 
This means in my view that the Rabbinic Council, of which Rabbi Green Chairs, ought to meet and formulate a program for synagogues to provide during Sukkot , Shmini Atzeret , Shavuot etc. for children to attend (hopefully free of charge except for fees for lunch and snacks). It would mean that synagogues provide programming for which parents register their children. It would mean synagogues would have to revive junior congregation and offer quality programming for at least a half day (or more possibly), such that parents who work those days could drop off their children on their way to work. There would have to be different programming for different age groups that is holiday related. For example, would it be possible for Len Udow at Temple Shalom to give a session on Jewish song? Could children participate in part of the regular service with the adults or have their own separate one?  Could the children play holiday charades or other games as part of special holiday programming? Could there be discussion groups on Jewish topics for older children?  Could the synagogues enlist the help of the two summer camps to help come up with fun holiday programming for the synagogues to offer on these days? Could there be sing downs or "shiria" or pantomime Camp Massad style? There may be Gray Academy parents or others who would volunteer and help supervise the special holiday programming, or who would be willing to lead related games or discussion groups. All of this would have to be organized by the synagogues.  
 
There is a golden opportunity here for synagogues to re-assert their role in the community by offering engaging holiday programs for children and teens who have days off from Gray Academy, such that parents drop the children off at the synagogue instead of going to the malls. There is certainly no harm in trying to plan this type of programming--and if there is good programming, they will come. (I think children would come especially if they knew some of their camp counsellors would be there).

If the synagogues need funding to develop this type of holiday programming for children then I would think there are options to be explored for funding (i.e. Synagogue Education Funds? The Jewish Federation? The Jewish Foundation?)