Tu Bshvat is bit of an evasive holiday. It has some elements of a Yom Tov but it is not quite there (for most of us anyway). Its Halachic ramifications pertain primarily to agricultural laws. Yet, the Magen Avraham (OC 573) indicates that while a chosson does indeed fast during the month of Nissan, he does not fast on Tu Bshvat because while the former is only a custom the latter has ties to the Gemara. Furthermore, we don’t say Tachanun or Tzidkusche Tzedek. There are also a few interesting widely accepted customs that include fruit, the sheva minim fruit and esrogim. What is Tu Bshvat? Is it a holiday or not? What is its significance?

We know that it is the New Year for trees. According to Bais Shammai the New Year occurs on Rosh Chodesh Shevat. Tosfos (Rosh Hashana 14a D”H Bechud) says that although they argue when it is celebrated, they both agree to its’ raison d'être. All fruits that blossom prior to Tu Bshvat (or Rosh Chodesh Shevat) are associated with the rainfall prior to that year and the fruits that blossom on or subsequent to Tu Bshvat (or Rosh Chodesh Shevat) are associated with the rainfall of that year. Hence, it is the New Year for trees.

The Meiri points out that Tu Bshvat marks the midpoint of winter. There are three months to winter; Teves, Shvat and Adar. Shvat is the middle month and Tu Bshvat is the midpoint of the month and consequently winter. After Tu Bshvat the cold weather starts to lose its strength thus allowing for the trees to blossom.

In effect, Tu Bshvat seems to be the midnight of winter. Midnight has a significant status in Jewish history. Look at the piyut in the hagadah: Vyhi Bachzi Haleiluh. There the paitan mentions many victories over our adversaries. When did they occur? - Vyhi Bachzi Haleiluh!

What is it about midnight that makes it so unique? Although midnight is in the midst of darkness, it is also the beginning of its end. It is the nexus between complete despair and the heartstring of hope.

Midnight is a dichotomy. It contains elements of both despair and hope. If you stop for a moment to contemplate, the night is quite essential for the light. Without darkness there is no light. Night serves as the contrast to light as deceit serves as the contrast to truth. The Midrash says that Truth was thrown to earth. Reb Zadok Hacohen in Rasisei leilah understands this to mean that truth can only function against the contrast of deceit. Humans are therefore the perfect vessels for truth. Angels do not have the capacity for truth because they do not have the capacity of deceit.

The paitan of Vyhi bachtzi halaila asks for Hashem to accelerate the process of reaching the time when there is no day or night. Kariev yom asher hu lo yom vlo leileh. This is referring to the days to come when everything is light and true. Without darkness there is no light.

Are midnight and midwinter analogous? Reb Zadok Hacohen in Kometz Haminchah says that before every Aliyah there lays a Yeridah. He quotes the Besh”t who learns the posuk in Mishle 24:16 “Seven [times] will the righteous fall and rise” to mean that nature was intended to share the same schedule; before day arrives, night appears and before the summer arrives, winter appears. Winter serves as the darkness for summer’s light as the night does for that of the day.

In the midpoint of the dark winter we see the light at the end of the tunnel. We ask Hashem to please speed up the process. Let’s see the geulah of Nissan. It is a quasi-Holiday in that we start to see the light of Geulah. However, we are stuck in the dark; the very medium that allows us to see the light. It is clear why we eat the fruit of the enlightened land in our golus. Why the esrog? The esrog is the flawless Tzadik. The esrog is also the fruit that is hadar; it has no yeridah it remains on the tree as the gemara says. It is what we aspire for during midnight. May Hashem bring upon us the light that makes us forget all darkness.