Rabbi David Teutsch once said two things about Judaism that stuck with me.  “Judaism is fundamentally counter-cultural and it is also fundamentally communitarian.”   There is no holiday where I find that to be more true than during sukkot.
If you haven’t been to Sukkahfest in the past 5 years at Isabella Freedman chances are you probably know someone who has.   Having just returned a few days ago as one of the organizers, I have heard two interesting bits of feedback about this popular annual retreat.  First, that it is prohibitively expensive.   Second, it is elitist and caters largely to Jewish professionals.  Both are valid critiques.   Sukkahfest is not cheap nor is it widely marketed towards a mass Jewish audience.   In most cases, you have to really want to be there to go.
What is Sukkahfest in a nutshell?   In short, it has become a festival for Jews who are committed to living out a full experience of the holiday in its different manifestations, especially as it relates to its ‘other’ names: Hag Ha’asif and Zman Simchateinu.  Sukkot customs urge us to remember and practice two crucial aspects of our lives not easily quantifiable.  The first being our vital connection to the land and that we depend on the fruits of the earth just as much today as we ever have.  But just as crucial is one of the more bizarre commandments.  As Pesach Stadlin said, “we’re commanded to sit in a shabby hut with our friends and be happy.” We are commanded to be happy.   Counter-culturally happy, one might say, since our joy is directly linked the simplicity and impermanence of the sukkah.    Essentially, we are commanded to be happy and be grateful.    That is, in large part, the purpose for the sukkah and the 4 species.  They are vehicles to help adjust our attitude toward the spirit of the holiday.
These are not simple mandates.  Happiness cannot be bestowed upon us.   True appreciation for things we take for granted cannot be ordered from a menu.  One must insert themselves in an environment conducive to waking us up to these states.   The tradition calls for all this to occur in a communitarian setting.   Joy and appreciation should be a group experience.
With that in mind, here are five examples of how I believe Sukkahfest succeeded in changing my mind-state to bring me closer to what I define as the true intention of the holiday.
1.   Singing and Praying:  Whether during prayer, before, during or after meals, there was an abundance of song outside, but especially under the sukkah.   Whether it was during Hallel, Havdallah, Birkat Hamazon, or someone teaching a 3-part round, the sound of dozens of Jews singing together was a constant.
2.  Being outside:   The Hoshanot section for one of the morning prayer options was done outdoors as an explicit affirmation of our dependence on the earth for sustenance.   Being in a parade of lulavim outdoors makes me wonder if the waving the lulav was ever meant to be an indoor activity.
3. Eating:  Virtually all the vegetables, cheeses and other ingredients used to make the food were grown and harvested by ADAMAH or local farms.
4. Immersing: Everyone was encouraged to eat their meals inside the sukkah and spend as much time there as possible.   There was almost never a moment when the sukkah was empty.
5. Dancing:  Spontaneous hassidic style circle dancing under the sukkah with over 100 people.  This took the communal Sukkahfest experience to a new level.  The simcha dancing in our sukkah paralleled the climax moments of a horah at traditional Jewish wedding.  I was left with this continuous feeling of simply not wanting to leave the sukkah for fear of missing the next great moment.
For those five reasons and many more, Sukkahfest worked.   While the above critique is valid, a counter critique could acknowledge how difficult it is to truly experience the holiday of sukkot in an urban setting without access to a real communal experience.   David Teutsch might be correct to assert that Judaism is fundamentally counter-cultural and communitarian, yet I fear the gap between theory and lived practice is a big one for many Jews today.   Sukkot, if we truly celebrate it, is the perfect holiday to begin to close that gap.
If retreats like Sukkahfest are financially prohibitive or overly elitist for much of today’s Jewish population, let us find alternative ways to celebrate sukkot.  May we renew our commitment to experiencing the radical communal joy this holiday can bring.