The Toothpick Appreciation Festival was held annually in Cotton Mouth Bluff. Three known events were held during the festival: the Toothpick Brawl-a-thon, the Toothpick 500, and the sharpshooting contest. Sheriff Toothpick himself hosted them, and his three toughest henchmen were the defending champions in the known events.
In Sly Cooper: Thieves in Time, Sly Cooper needed to break "Tennessee Kid" Cooper out of jail in order to restore his reputation as the greatest outlaw of the Old West. The one way for this to work involved Sly getting thrown into the clink himself, so he went on a crime spree. The last crime that he committed was taking down the banner for the Toothpick Appreciation Festival.
Later in the game, the Cooper Gang had to stop Toothpick from transporting the gold he had stolen from the mines. They made note that Toothpick's train was supercharged by the Cooper Van, and they needed to recover it so they wouldn't be stranded in Cotton Mouth Bluff. The best way for them to do that was to divert the route of the train. However, in order to do this, they needed three keys, which Toothpick's toughest henchmen all kept very close by themselves. The only way for them to obtain the keys was by challenging Toothpick's henchmen in the festival's events.
The Toothpick Brawl-a-thon was set in a hand-to-hand combat arena with a net surrounding it. The point of the event is to win out over incoming challengers. Wildman Weezner was the defending champion.
Murray participated in the event for the Cooper Gang. He first had to knock out twenty coyotes, which he did with great success. After this, Wildman arrived in the arena, ready to challenge Murray who was too strong for Wildman who then coughed up the key as Murray sucker punched him into the air.
According to Bentley, the Toothpick 500 gets its name from how many people have met their deaths on the course. The event is set on an obstacle course littered with explosives and signs that show the racers where to go. In order for a participant to remain in the event, a checkpoint must be passed within the right amount of time. The point of the event is to cross the finish line in the fastest amount of time. Frenchie Le Stashe was the defending champion.
Sly Cooper participated in the event for the Cooper Gang. The only way for him to be able to beat Frenchie's time was by rolling on the ball from his Jailbird Costume. After dodging many obstacles, Sly finally crosses the finish line, faster than Frenchie's best time. The jackalope threw a fit, and in doing this, he shook the key out of his pocket.
The sharpshooting event is set in a room with standing grounds at a considerable distance from an area where targets pop out of slots. The point of the event is to score the most points before time runs out. Red Eye Robles was the defending champion.
Carmelita Fox participated in the event for the Cooper Gang. After coming in late, she made a deal with Red Eye that if she won, he had to hand over the trophy, and if she lost, she had to kiss him. Carmelita's score went higher than Red Eye's did, who claimed that she had used some kind of magic to beat him. Carmelita took the trophy, which had the key inside, with her.
After collecting all three keys, the Cooper Gang diverted Toothpick's train and thwarted his plan to transport the gold. Toothpick was arrested by the western authorities and sentenced to work on the railroad with a chain gang. Because of this, the Toothpick Appreciation Festival was ended permanently ever since.