Holiday Scavenger Hunt
This one is a bit weather-dependent, and requires some planning — but we've tried it and it is beyond fun.

Have everyone contribute a small sum of money, then plan a large-scale scavenger hunt around town leading up to an awesome group prize (concert tickets, straight-up cash, a set of cool lipsticks...you decide!). This works best with a close group of friends — the places and activities can be inside jokes or memories. The planner creates a checklist of activities that must be completed and distributed to the players. Remember, this isn't a treasure hunt, so you don't need clues — just various activities that they need to check off a list. You can create teams among the group and whichever team finishes first, wins the prize — but it's also equally fun to do it just for the experience! And please, don't include anything that requires driving — everyone will be having too much fun to be worrying about road safety.

Image via Google Maps.