This is "Ice Race with Cory and Ashley" from Lostbets.com
This site has terrible load times for me, but has the scene of the actual challenge, but cuts out right before the punishment. http://www.tubecup.com/channel/lost-bets-games/169278/
Edit: Found an HD video download of the full thing: http://rapidgator.net/file/5217b9f4dff5fb687f19b839d3f5dde3/
it was something like this deal