In the years when I was first learning about Orthodoxy, I'm thankful I was able to participate quite a bit in various services throughout the seasons, so that I got a good foundation in how the intellectual knowing is the lesser part of a relationship with God. With every year that passes I see this more, and also feel my inability to convey in words this Reality that is Christ in His Church. Even the most eloquent and holy men and women would communicate by their entire persons, and relatively little by words, the Love that has been shed abroad in their hearts.
Still, their words are more eloquent than mine and express a deeper grasp of the realites by far, so I am depending on them to tell a little of how the day-to-day structure of the Church Year gives the grace of God. It all flows from the Resurrection. From the Orthodox Church in America site:
Although the first of September is considered the start of the Church year, according to the Orthodox Church calendar, the real liturgical center of the annual cycle of Orthodox worship is the feast of the Resurrection of Christ. All elements of Orthodox liturgical piety point to and flow from Easter, the celebration of the New Christian Passover. Even the "fixed feasts" of the Church such as Christmas and Epiphany which are celebrated according to a fixed date on the calendar take their liturgical form and inspiration from the Paschal feast.
Next week we have the Leavetaking of Pascha, which I love very much, because it always seems to me that I haven't been able to sing enough times those exultant hymns of "Christ is risen from the dead, trampling down death by death." Every year I become more familiar with some of the words and tunes, and try to learn a new one. "Why seek ye the living among the dead? Why mourn ye the incorrupt amid corruption?" On Leavetaking of Pascha we'll repeat the Easter service in its entirety - and then won't sing those hymns again until next year.
Even though we will still be in "the time of Easter" for another ten days, until Pentecost, we must say good-bye to the Feast of Feasts, so to speak, because we are coming up to the Ascension! Then we will update our greeting from "Christ is risen!" to "Christ is ascended!" the response to that being, "...from earth to heaven!"
In his book, The Year of Grace of the Lord, Fr. Lev Gillet tells at length the meaning of the Church Year. An excerpt from one paragraph, to which I have added breaks to make it more readable on the screen:
The liturgical year is, in fact, expressed as a calendar, but simply to identify it with a calendar would be totally inadequate. One could also say that the purpose of the liturgical year was to bring to the minds of believers the teachings of the Gospel and the main events of Christian history in a certain order. That is true, but this educational, pedagogical, function does not exhaust the significance of the liturgical year.
Perhaps we could say that its aim is to orient our prayer in a certain direction and also to provide it with an official channel which is objective, and even, in a certain way, artistic. This, too, is true, but the liturgy is more than a way of prayer, and it is more than a magnificent lyric poem.
The liturgy is a body of sacred "signs" which, in the thought and desire of the Church, have a present effect. Each liturgical feast renews and in some sense actualizes the event of which it is the symbol; it takes this event out of the past and makes it immediate; it offers us the appropriate grace, it becomes an "effectual sign," and we experience this efficacy to the extent that we bring to it a corresponding inclination of our soul.
But still, this does not say everything. The liturgical year is, for us, a special means of union with Christ. No doubt every Eucharist unites us intimately with Christ, for in it he is "both he who offers and who is offered," in the same way that every prayer, being the prayer of the members of the mystical body, shares in the prayer of him who is the head of the body and the only one whose prayer is perfect.
But, in the liturgical year, we are called to relive the whole life of Christ: from Christmas to Easter, from Easter to Pentecost, we are exhorted to unite ourselves to Christ in his birth and in his growth, to Christ suffering, to Christ dying, to Christ in triumph and to Christ inspiring his Church. The liturgical year forms Christ in us, from his birth to the full stature of the perfect man. According to a medieval Latin saying, the liturgical year is Christ himself, annus est Christus.