This year, Tu B’Shevat, the 15th day of the month of Shevat, occurs on Sunday Eve, Feb 5 and Monday, Feb 6.
The day is significant because, by this time, most of the winter rains have fallen in the Land of Israel, promising a summer of luscious, delicious fruits for which Israel is praised. For this reason, Tu B’Shevat is also considered Rosh Hashanah (the New Year) for fruit trees regarding certain Halachot of agriculture.
The Torah likens man to a tree, "For man is a tree of the field" (Deut. 20:19), but this isn’t an insult! Instead, humans are like trees in that our head is rooted in the Heavens, nestled in the spiritual soils of the Eternal, and nourished by our connection to our Creator. Our arms and legs are like branches, through which he accrues good deeds, and upon which the "fruits" of our labor are laden. Therefore on Tu B’Shevat, one must revitalize his connection to G-d, and rejuvenate his commitment to keep the mitzvot (Midrash Shemuel on Pirkei Avot 3:24).
It is the custom on Tu B'Shevat to eat from the seven species for which G-d praised the Land of Israel: "...a land of wheat and barley and [grape] vines and fig trees and pomegranates, a land of olive trees and [date] honey" (Deut. 8). According to the Kabbalists, the custom in the Land of Israel is to eat fifteen different types of fruits, corresponding to the 15th of Shevat. By increasing the blessings we pronounce over G-d's produce, we become more aware of His providential role in creation. Not by our toil alone does the land bear fruit. Without G-d’s providing rain and sustenance, the farmer's efforts would be worthless.
The Kabbalists also made a sort of "Seder Night" on Tu B'Shevat, over four cups of wine. The first cup is of white wine, symbolizing the pale slumber of winter. For the second cup, red wine is added to the white, symbolizing Creation’s stirring from winter’s slumber. The third is of more red wine than white, heralding the gentle warmth of spring. The fourth cup is completely red, representing the strength of the coming summer sun. On a personal level, this expresses our desire to rekindle our spirituality. It also represents the transition between this world of relative spiritual paleness and the world to come of great spiritual intensity. On a collective level, it represents the cold "lifelessness" of exile that contains within it the seed of redemption and the blossom of Mashiach.
Wishing you all the best!
Rabbi Sholom Mimran