Blessed John Henry Newman begins one of his sermons on the season of Advent by noting the stark chill of December: “The year is worn out,” he says, “spring, summer, autumn, each in turn, have brought their gifts and done their utmost; but they are over and the end has come.” There’s something about these days of increasing darkness that naturally puts us in the frame of mind to consider the future, to consider the passing of all things. “These are feelings for holy men in winter and in age,” says Newman, “waiting, in some dejection perhaps, but with comfort on the whole, and calmly though earnestly, for the Advent of Christ.”
Advent is a season particularly for those intent on Christ, intent on their relationship with him in this world so as to enjoy the promises of the next. Again, from Newman:
The season is chill and dark, and the breath of the morning is damp, and the worshippers are few, but all this befits those who are by profession penitents and mourners, watchers and pilgrims. More dear to them that loneliness, more cheerful that severity, and more bright that gloom, than all those aids and appliances of luxury by which men nowadays attempt to make prayer less disagreeable to them.
In short, the liturgical season of Advent is the preferable season for the wayfarer, the pilgrim, in this world, especially those consecrated to be eschatological signs of the life to come. This is our season.
From: homily Father Thomas Petri O.P. in First Things