Cowboy Hat Toss
To play this game, you need a hula hoop and a volunteer. Tell the volunteer to stand about five feet away from a starting point. Give him the hula hoop and have him hold it at his side at about hip-height. Line up the rest of the players at the starting point and give the first player in line a cowboy hat. To receive a point, he must throw the cowboy hat through the hula hoop. Let everyone have a turn, and then move the volunteer another foot away from the starting point. Have everyone continue to throw the hats through the hula hoop with the volunteer moving back a foot after every round. The person with the most points at the end of the game wins.
Clumsy Cowboys
Divide the players into two teams and line each team up at a starting point. Parallel to both teams at the opposite side of the room, place two chairs. Place an oversized cowboy hat on the top of each of the first players' heads. When you say "Go," the first players have to race to the chairs on the opposite side of the room, run around their teams' chairs and then head back to their teammates. As soon as they get back to their team, they pass the cowboy hat off to the next player in line. If a player's cowboy hat falls off, he has to put the hat back on and continue the race. The first team to have all of its players back in line wins the game.
Cowboy Limbo
A cowboy twist on the classic limbo game, have two people hold the ends of a long pole. Line up all of the players behind the limbo stick and place a cowboy hat on top of the first player's head. Hold the limbo stick at shoulder-height to start out with, and have each player make his way under the stick with the cowboy hat on his head in the first round. Any player who touches the limbo stick with his cowboy hat gets eliminated. After every round, place another cowboy hat on the players' heads and lower the limbo stick. The last player standing wins the game.