Types of Medieval Entertainment varied according to status but included festivals,feasts, banquets, Mystery Plays, fairs, games and sports, hunting, hawking, animal entertainment using dogs, bears and monkeys.
Nice article here:
http://www.lordsandladies.org/entertainment-middle-ages.htm
Should our protagonist observe and/or participate in such activities as sort of mini-games. Some of them involve gambling and a potential for payout. Some of them would be used to gain reputation or slowly increase your stats like intelligence or agility.Invest in a side-business perhaps. Discuss