With the amount of lore research they are doing/have done for this game, I can't see them skipping over a simple in-game lore based calendar system. We'll probably have in-game holidays, with gaming events, that center around it!
As for what holiday I'd like to see:
* Last Seed 27th Harvest's End Perhaps no other festival fires the spirit of %cn as much as the one held today, Harvest's End. The work of the year is over, the seeding, sowing, and reaping. Now is the time to celebrate and enjoy the fruits of the harvest, and even visitors to this region are invited to join the farmers. The taverns offer free drinks all day long, an extra vagance before the economy of the coming winter months. Underfed farm hands gorging themselves and then getting sick in the town square are the most common sights of the celebration of Harvest's End. That sounds like it could turn into an AWESOME in-game event!
~Evarwyn
*The above comes from the Skyrim Wiki: http://www.uesp.net/tamriel/society/tamholi.shtml#frostfall