Originally Answered: Games/Entertainment/Festivals in Medieval times? (Dark Ages, Middle Ages)?
In 'Life in a Medieval Village' Frances and Joseph Gies write:
'many of the games enjoyed by the villagers were played alike by children, adolescents and adults, and endured into modern times: blind man's buff, prisoner's base, bowling. Young and old played checkers, chess, backgammon, and most popular of all, dice. sports included football, wrestling, swimming, fishing, archery, and a form of tennis played with hand coverings instead of rackets. The Luttrell Psalter (c. 1340) portrays a number of mysterious games involving sticks and balls and apparatus of various kinds, remote ancestors of modern team sports. Bull-baiting and cockfighting were popular spectator sports.'
'Football' as mentioned above is the game known in America as 'soccer', and tended to be a very rough game in medieval times, with loads of men playing on both sides, and serious injuries not an unusual occurence.
Dancing of course was a popular form of entertainment. In 'Pleasures and Pastimes in Medieval england' Compton Reeves writes:
'Dancing at the amateur level was ordinarily round-dancing or processional, and was of ancient lineage. Carols were the principal form of secular music in medieval england, and they are the musical core of the entertaining chain-or carol-dance. The carol-dance was usually performed by a circle of dancers, with hands clasped or arms linked, who would take a a few steps to the left as their leader, normally standing in the middle of the circle, sang a stanza of a song. The dancers then marked time with treading steps as all sang the chorus (or burden). This basic dance could be varied in many ways, from dancing in line to miming the story of the carol, and the carols might be stories abour heroism, romance, or religion. for the most part, carols seem to have been joyful. Carolling could be done outdoors, and the churchyard was a favourite venue, or indoors in a lordly hall.
The carol-dance was not the limit of dancing activity. The basse dance was performed on the ground without springing into the air, and was a late medieval refinement of the processional dance or open carol-dance. The pavane was a fast-moving variation on the basse dance, and called for displays of many manners of steps and elaborate costumes.'
There are lots of recordings of medieval music available, so a carol dance might be a nice thing to arrange.
Another thing that might be exciting to do would be a medieval 'mystery' play. These were normally stories from the bible or the lives of the saints, and were often performed by the members of medieval trade guilds at special times. There are scripts of medieval mystery plays available. You could do the story of Noah's Ark, for example, which is usually very amusing, or perhaps part of the Nativity. There is a comic scene in some versions of the Nativity which involves a sheep stealer who steals a sheep and when the other shepherds come looking for it he pretends it is a baby and puts it in a bed.