The Deep Joy of Sukkos

By Rabbi Pinchos Lipschutz

Sukkos, the Yom Tov of simcha, comes to us like a sun-drenched mountain after a long and hard climb. After the awesome days of the Yomim Noraim, when our souls were laid bare, our hearts taken over by yearning and tefillah, we emerge into the warm embrace of a Yom Tov whose very essence is joy. As the posuk declares (Devorim 16:14-15), “Vesomachta bechagecha vehoyisa ach someiach — And you shall rejoice in your festival, and you shall be only joyful.”

Only joyful.

How can such a command be fulfilled? Is it possible — after weeks of intense introspection, of confronting mortality, sin, and judgment — to cast the seriousness aside and rejoice, wholly, deeply, uninterruptedly?

The answer is whispered in the leaves of the sukkah, in the rustle of the s’chach above our heads, in the fragile walls that seem to tremble with eternity.

Yes, says the Torah. Yes, says the Zohar. And yes, says the Jewish soul.

Because this joy is not an escape from the seriousness of life. It is its reward.

The Zohar (Parshas Emor) reveals a breathtaking secret. During Sukkos, Hakadosh Boruch Hu comes to dwell with His beloved children in their humble sukkos. He does not demand palaces of marble or ivory. He does not wait for golden thrones or ornamental crowns. No. Hashem comes to the sukkah. The imperfect, breezy little sukkah. And He rejoices there with us.

What greater joy could there be than this? The Creator of the universe, the Master of all worlds, comes to sit beneath our s’chach, to bask in our love, to envelop us in His presence.

The Vilna Gaon, whose insights blaze like lightning across the heavens of Torah, would say that the most difficult mitzvah is not shiluach hakan, nor the depths of korbanos, nor anything that we would imagine.

The hardest mitzvah, said the Gaon, is the one that obligates us to be completely joyous on Sukkos, without any hint of sadness or distraction. Not just happy in theory. Not just smiling on the outside, but fully, truly, spiritually joyous.

Can we do it?

A young man who learned in the famed Volozhiner Yeshiva, the beating heart of Lithuanian Torah life, wrote a diary that was found and printed. His words transported me. I want to share them with you. He wrote:

“The small towns of Lita were solemn a whole year round; there was no income, and poverty was all they knew. But when Yom Tov arrived, old, dark bread was replaced with white bread, and everyone wore freshly cleaned clothing. Yom Tov brought a tremendous change. Everything was different. It felt like going from darkness to great light.”

Just pause for a moment. Imagine it. A shtetel cloaked in the grey of struggle suddenly transformed. The children run through the narrow streets with shining faces. Fathers who’ve worked all year for mere kopeks now wear pressed white shirts. And even if there’s just one chicken for the whole Yom Tov, it’s shared with laughter and song.

He continues: “During the Yom Tov of Sukkos, the town of Volozhin was adorned. All its inhabitants were swept up in celebration. The yeshiva bochurim sang and the cheder children danced around so merrily. From every corner of town, there was heard only much joy and happiness, as the town of Volozhin was overcome with rejoicing and festivity.”

Can you hear it? The singing? The joy? The walls of the sukkos glowing in the candlelight, as old and young sit shoulder to shoulder, sharing divrei Torah and perhaps singing niggunim?

And then, his final lines, bursting with emotion:

“This was true of all the Lithuanian shtetlach, but was most pronounced in Volozhin due to the presence of so many yeshiva bochurim. All year, they were in a different world — the world of learning. But when Sukkos came, their inner happiness burst forth and they added even more to the city’s exultation.”

Because Sukkos isn’t only about outer joy.

It’s about letting the joy that lives deep inside us emerge.

Let us now dive deeper.

The Torah tells us (Vayikra 23:42-43), “You shall dwell in sukkos for seven days…so that your generations will know that I caused the Bnei Yisroel to dwell in sukkos when I took them out of Egypt.”

Something is puzzling here.

The Torah doesn’t say “so that you will remember” as it does by other mitzvos. Regarding tzitzis, it says, “Lema’an tizkeru — so that you will remember.” Regarding Pesach, the same. So why, here, does it say, “Lema’an yeidu — so that they will know?”

Because Sukkos is not only about memory. It’s about knowing. Not history, but presence. Not nostalgia, but experience.

We are not merely commemorating something that once happened. We are stepping into it.

We are reliving the moment Hashem enveloped us in the clouds of His love. Every year, when those hashpa’os are evident, we relive the time of Hashem’s return.

The Tur asks a question that has often been repeated since he posed it: If Sukkos commemorates the Ananei Hakavod, the holy clouds that surrounded the Jewish people when they left Mitzrayim, why don’t we celebrate Sukkos during Nissan, when the Jews left Mitzrayim? Why do we celebrate it during Tishrei?

The Vilna Gaon (Shir Hashirim 1:4) gives a stunning answer. He says that the sukkah we build does not commemorate the original Ananei Hakavod that came after Yetzias Mitzrayim. Instead, it celebrates their return after they were taken away.

When the Bnei Yisroel sinned with the Eigel Hazohov, the clouds, the Shechinah, and the Divine intimacy departed. But then Moshe Rabbeinu ascended Har Sinai again to beg for forgiveness. On Yom Kippur, he descended with that forgiveness in hand.

And then, from the 11^th to the 14^th of Tishrei, the people gathered materials for the Mishkon, demonstrating their renewed commitment. On the 15^th of Tishrei, construction of the Mishkon began.

And the clouds came back.

That is what we celebrate on Sukkos.

Not just the kindness of Hashem in protecting us, but the return of His love after we fell.

This understanding gives new meaning to the calendar.

On Rosh Hashanah, we proclaim Hashem’s kingship. During the Aseres Yemei Teshuvah, we repent and plead for mercy. On Yom Kippur, we are forgiven and cleansed. And then comes Sukkos.

Sukkos is the embrace.

It is Hashem saying, “Come back to Me. You are Mine, and I am yours.”

The Ramchal (Derech Hashem 4:7) writes that the light of the original Anonim reappears during Sukkos. Their power — the safety, the clarity, the closeness — is awakened again in our generation.

That means that when we sit in the sukkah, we are not just in a symbolic booth.

We are sitting in a space that echoes with Divine protection.

Unlike most mitzvos, where performance is the obligation, the sukkah requires not just sitting, but also building.

The Rama (Orach Chaim 624:5) teaches that righteous Jews begin building their sukkah immediately after Yom Kippur.

Why?

Because when a mitzvah comes to your hand, don’t delay it. “Al tachmitzena.”

But there is more.

When we build the sukkah, we are not merely erecting walls.

We are building a dwelling place for the Shechinah. A mikdosh me’at. A sanctuary. A home for Hashem in this world.

That’s why it matters how we build it. With kavonah. With thought. And of course, with joy. With hands that have just been purified in the fires of Yom Kippur.

A sukkah is a statement: “Hashem, I want You in my life.” As we proclaimed on Yom Kippur, “Ki anu bonecha v’Atah Avinu. Anu amecha v’Atah Elokeinu.” We are Yours.

The Be’er Heiteiv (639:1) quotes that building the sukkah is akin to being a partner with Hashem in the act of creation.

How so?

Because just as Hashem created a world in which His presence could dwell, so too do we — the newly cleansed Jewish people — create a small world, a sukkah, where He can reside once again.

The Shechinah, says the Zohar, rests in every sukkah built l’sheim Shomayim.

Even the simplest ones. Even yours.

Even the ones with plastic chairs and worn-out boards. The ones that leak and let in cold winds through the cracks. The ones with the latest decorations, the ones with last year’s signs, as well as the sukkos with no decorations at all.

If it’s built with love, determination and dedication to the mitzvah, Hashem is there.

Chazal use a breathtaking term for the sukkah: “b’tzeila demehemenusa — the shadow of faith.”

What is faith if not trust in what you cannot see, in what transcends your control? The sukkah, by halachic definition, must be a temporary dwelling. It sways in the wind. It leaks in the rain. It’s fragile — on purpose.

And that’s exactly why it becomes a place of deep serenity.

Because it teaches us that real security doesn’t come from brick and mortar.

It comes from emunah.

It comes from knowing that the very same G-d who held our ancestors in His Clouds of Glory in the desert surrounds us now — with no less love, with no less care.

The flimsy walls are stronger than steel when Hashem stands beside you.

The s’chach above your head? It may look like leaves, but spiritually, it’s the canopy of the Divine.

In a world spinning with uncertainty, where we grasp for control, where so much is unpredictable and so many are unfriendly, the sukkah invites us to let go, to lean in, and to know.

To know that He is with us.

And just when the sukkah feels most personal, most intimate, something else happens.

On each night of Sukkos, we welcome seven exalted guests, the Ushpizin, into our sukkah: Avrohom, Yitzchok, Yaakov, Yosef, Moshe, Aharon, and Dovid Hamelech.

Why?

Because their lives were comprised of challenges and trust.

Avrohom left everything behind to follow the voice of Hashem. Yitzchok was forced to leave home. Yaakov slept with his head on stones, running from Eisov. Yosef was sent into golus by his brothers. Moshe lived between palaces and tents, chased by kings and carried by prophecy. Aharon was involved in the Eigel story and lost two of his four sons on the day Klal Yisroel celebrated the consecration of the Mishkon. Dovid Hamelech spent much time not on a throne, but in caves and in exile.

When the Ushpizin come into our sukkah, it’s not as historical guests, but as teachers, as guiding lights with a permanent connection to Hakadosh Boruch Hu.

They sit beside us and remind us that when we are in the sukkah, we are not alone.

Let’s return to the Vilna Gaon’s statement: Sukkos is the most difficult mitzvah because it requires complete joy — and only joy.

Why is that so hard?

Because most of us live with tension, loss, disappointment, and unanswered questions. The world is heavy. Life is complex.

But perhaps Sukkos doesn’t demand that we ignore our struggles.

Perhaps it’s asking something more subtle and more profound: That after we have confronted our darkness during Elul and the Yomim Noraim, after we have faced our failures and cried out to Hashem with broken hearts, we are now invited to rejoice — because of that journey.

Sukkos is the joy that comes after teshuvah, not despite of it.

It is the joy of reconciliation. Of returning. Of being forgiven. Of being loved.

Imagine a child who ran away from home, hurt his parents, and rebelled. Then, one day, he knocks on the door, tears in his eyes. His mother throws her arms around him. His father kisses his forehead.

Now imagine the joy of that first Shabbos back at the table.

That is Sukkos.

In the times of the Bais Hamikdosh, Sukkos brought about the most awe-inspiring celebration ever known: the Simchas Bais Hasho’eivah. Chazal say (Sukkah 51a), “Mi shelo ra’ah simchas Bais Hasho’eivah lo ra’ah simcha miyomov — Whoever did not see the rejoicing at the Bais Hasho’eivah has never seen real joy.”

What made it so joyous?

It wasn’t a sumptuous meal. It wasn’t wine or bourbon. It wasn’t wealth.

It was water.

Simple, pure, tasteless water poured upon the mizbei’ach, elevated to holiness.

Because when you’re connected to Hashem, even water — even the simplest parts of life — is enough to dance over.

This, too, is the message of Sukkos.

You don’t need much to be joyous.

You need meaning.

You need clarity.

You need to know that Hashem is near.

And then, even a sukkah, with its temporary walls and a folding table, becomes the most glorious palace.

That is the arc of Tishrei. Rosh Hashanah awakens us to Hashem’s kingship. We are awed and stirred, fighting for our lives and everything that we need and hold dear.

Yom Kippur breaks us open. We are raw, cleansed, and sincere.

And then Sukkos lifts us. We are held, embraced, and surrounded by joy.

It is the joy that comes after winning a tough case, the embrace after the apology. It is the sunshine after the storm, the dawn after the long night.

This is the joy that broke through the poverty of Lita, that filled the diary of a Volozhiner bochur with wide-eyed awe.

This is the joy that turned wooden huts into spiritual sanctuaries.

The joy of Sukkos.

Sukkos, when we step inside the sukkah with reverence and sit with our families, neighbors and guests. We make Kiddush, recite the Shehecheyonu thanking Hashem for keeping us alive, eat a kezayis of challah, are careful with our speech, and remember that beneath the fragile roof, we are under the wings of Hashem’s protection.

How can we not be filled with simcha? After the Yomim Noraim, we are duty-bound to feel joy, for failing to do so would mean ignoring the immense blessings bestowed upon us with the Yomim Noraim. Nothing should be able to shake us and upset us.

When we are home with Hashem, we are reminded that He causes everything to happen and nothing that we experience happens on its own. Challenges that we face are placed there by Hashem to strengthen and improve us. It is all for the good.

May that knowledge bring us to simcha. Deep and lasting simcha.

May the clouds of Hashem’s Glory return in their fullest form with the coming of Moshiach speedily in our days.

Ah gutten Yom Tov.