The Labyrinth of Ariosto is perhaps the oldest known role-playing game; it was created by prince Thomas of Savoy and based on Orlando Furioso (1516). Twelve players were needed; every player chose the name of one of the characters in the poem: Orlando, a knight, a princess, St Michael, Charlemagne, Neptune, Merlin, a dwarf, an amazon, Pegasus,… The players moved on a board of 335 squares representing various episodes in the poem; they fighted and reenacted some passages from the book and managed to escape the labyrinth. Players of great culture were needed, as it was a very complex game.
As can be seen in the wonderful book by Alfredo Aracil (Juego y artificio (Game and artifice). Madrid: Cátedra, 1998, 202-3), the author mentions the game as cited in a work by François Menestrier, Des ballets anciens et modernes, selon les règles du théâtre. Paris, 1682, 308-309.
I found an interesting article on this topic:
I also found a brief report in the 16th century concerning the current concept of online adventure games. This is a great feast prepared by Queen Mary of Hungary, governor of the Netherlands, to honour the young crown prince Philip of Spain. The event took place in 1549, in the Belgian town of Binche. The queen had a homemade planetarium in a room: planets hung from the ceiling and stars glittered in the dark; some mechanisms, activated by the servants, could bring rain, hail (candies, of course), thunder and lightning in the room (Aracil, op. cit, 238).
In the castle, a chivalric-romance-style game was organized; every player chose a character, and the leading role was played by a 22-year-old prince. There were enchanted swords, fights in a tenebrous castle and artificial storms. Yes, you guessed right: the prince won.The game lasted two days; it is cited in El felicíssimo Viaje d’el muy alto y muy Poderoso Príncipe Don Phelippe, Hijo d’el Emperador Don Carlos Quinto Maximo, desde España a sus tierras de la baxa Alemaña; con la descripción de todos los Estados de Brabante y Flandes, Amberes, 1552. The autor is J. C. Calvete de Estrella; the work was edited by the Sociedad de Bibliófilos españoles, Madrid, 1930 (vol II, 67-68, 29-50), as I learnt from Aracil’s work.