The Oregon Trail is both entertaining and educational. Sadly it's also quite old, and in need of an update. An update like Thule Trail, which takes the basic premise of the Oregon Trail but has you and your mates on a cross-country road trip to a festival, and includes truck-stop hookers, dice games, hybrid sedans and whiny hitch-hikers. Thule Trail's broswer-based, so you can try it out at the link below.
Thule Trail [via Independent Gaming]

Send an email to the author of this post at plunkett@kotaku.com.