When Jack and his son Charlie are riding the toboggan (to get away from the bullies), Jack breaks the toboggan into two halves and Jack and Charlie ride separate halves down the hill. When they reach the bottom, Charlie is on a real snowboard, not half of the toboggan.
The tour sheet on the fridge shows the Denver concert as the 22nd. Next day (23rd) Charlie arrives home from school, and Jack is still traveling home. 24th is Charlie's hockey game, and that night Jack says to head to the cabin. The next day,25th, while packing, Jack gets a phone call to perform "Tomorrow", to which Gabby states is Christmas Day.