Advent has historically been seen by the Church as a season of fasting and penance, so its customs are in keeping with that mood of self-restraint. There aren’t many old Advent traditions from Britain; most current Advent customs, including Advent calendars and wreaths, are of German origin.
Saints’ days are exceptions to the penitential mood, though. The best-loved feast in Advent has long been St Nicholas’ Day on December 6. St Nicholas is patron saint of children (among many other things), and lots of European countries have traditions associated with his feast. One is the custom of leaving presents in children’s shoes, which was taken to America by German and Dutch immigrants – and there St Nicholas, “Sinterklaas”, became Santa Claus.
On the feast of St Nicholas in medieval England, many cathedral choirs would elect a chorister as Boy Bishop. The Boy Bishop would wear vestments, lead processions, and give sermons. His reign would last until Holy Innocents’ Day. This was a playful festive role-reversal, as well as a gentle reminder to the adult clergy of Christ’s injunction to become like a little child to enter the kingdom of heaven.
December 21, the feast of St Thomas the Apostle, was once the day for a widespread custom of charity. Poor women would go house-to-house asking for a small dole of money or food to help them feed their families at Christmas. The practice was called “gooding” or “Thomasing”. Because it’s the winter solstice, the shortest day of the year, they would sing: “St Thomas grey, The longest night and the shortest day, Please to remember St Thomas’ Day.”
The last days of Advent are the season of the “O Antiphons”. These texts, sung at Vespers, appeal to Christ under different titles, asking him to come and save his people. In medieval monasteries, each antiphon would be sung by a monk with an appropriate role: “O Root of Jesse” by the gardener, “O Key of David” by the cellarer, and so on. These ancient antiphons are still popular today as the hymn “O Come, O Come Emmanuel”.