Each Wanderer has a specific set of requirements you must meet in order to race them. Some are simple, some are harder. You must figure out what each wanderers requirements are. Some are based on wins, some on money, some on cars owned, etc. Many of them have to do with the day you are on. For example, some only race on days that are multiples of 7 (or other numbers) while others only race past a certain amount of days. Good luck!