Jockey Pablo, Farmer Tyrone, and Cowgirl Uniqua enter a horse race in Kentucky, starting from the horse racing stadium, and going all the way to the Mississippi River, but Uniqua and Pablo keep 'horsing around' and showing off their skills instead of racing. Will Farmer Tyrone win the race?
Uniqua is in the backyard wearing a beige cowgirl hat. She introduces herself to the viewer as Cowgirl Uniqua, a horse rider who loves to race. She happily starts singing The Horse-Ridin' Cry as she tells the viewer that she is the best horse rider of all time. Pablo, wearing a jockey helmet, walks over and introduces himself to the viewer as Jockey Pablo, another skilled horse rider who has won every race he has competed in. He calls himself the best rider ever. The two riders meet and start declaring themselves to be the best. Pablo joins in as they resume singing The Horse-Ridin' Cry. They challenge each other to a race to prove who is better.
The backyard transforms into a stadium. Austin wearing a news reporter outfit holds a microphone up to his mouth and announces "Ladies and gentlemen, welcome to the races!". Uniqua and Pablo ride their horses onto the racetrack, still debating who will win. Uniqua and Pablo suddenly hear a sunny voice greet them. They look around until they realize that Tyrone is sitting on a donkey, right between them both. They ask what he is doing there, and he answers by telling them that he is a contestant in the race. Tyrone introduces his burro as Molasses. Pablo and Uniqua laugh sweetly. They both think Molasses is cute, but they doubt he'll be able to beat their horses in the race.
Austin exclaims that the race will start. The horses race out of the stalls as Tyrone and Molasses remain perfectly still in their own stall. Jockey Pablo and Cowgirl Uniqua begin singing When I Win. Austin happily announces that Uniqua and Pablo have left the stadium, while Tyrone hasn't moved an inch. Tyrone tells Molasses that it is okay and that they should take their time.
Riding out of the stadium, Jockey Pablo and Cowgirl Uniqua feel confident that there's no way Farmer Tyrone will catch up with them, let alone win. Back at the stadium, Tyrone and Molasses move a few feet from the stalls, singing When I Win. Meanwhile, back outside the stadium, Pablo and Uniqua start talking about who can ride the fastest. Uniqua points out that she's ahead by a nose, then Pablo rides ahead and says that now he's the one ahead by a nose. They keep passing each other, by two eyes, a neck, until Pablo stands up on his horse. Uniqua stands up on her horse, and balances on one leg. Jockey Pablo comments that it's easy when going in a straight line, but not so much if the horse is going in circles. Pablo and Uniqua start turning around on their horses and start to get dizzy. During this time, Farmer Tyrone and Molasses pass them. "Don't forget about the race! Remember, the Mississippi River's that way!" he tells them.
Jockey Pablo and Cowgirl Uniqua remember the race and resume their riding. Within seconds, they pass Farmer Tyrone and Molasses. "Just keep on goin'!" Tyrone tells her.
Meanwhile, Uniqua and Pablo, approach a barnyard. Austin struggles to tell who is in first lead. After jumping over a log in the road, the two begin debating over who jumped the highest. They start bickering until Uniqua spots the outer fence of the barnyard. She challenges Jockey Pablo to jump over the fence to determine who's the best jumper, but after that, they enter the barnyard and begin a jumping contest, daring each other to do dangerous jumps. They sing I Betcha as they bet on who can do what. They compete against each other on various jumps: They jump over a tree, a lake, a pile of hay, and a fountain. By the end of the song, Molasses and Tyrone pass the barnyard. Uniqua and Pablo, who are still betting on who can do which jumps, notice they've been passed again. The horse riders pause and then get back on the main road since they don't want to lose to a small slow burro. They immediately pass the donkey and the moose. Tyrone tells Molasses not to worry and they should just see how it turns out.
Meanwhile, the pro horse riders have come across a mountain. Jockey Pablo tells Uniqua that haven't detemined who's the best climber in the world. They bet each other can't climb it. Then they bet each other that they can't do it without their horse, can't climb it without their hands, and can't use their feet, either. Reaching an agreeable solution, Pablo and Uniqua decide to scoot up the mountain backwards while whistling. Austin the announcer expresses his complete and utter disbelief at what he's watching, and announces that if Jockey Pablo and Cowgirl Uniqua don't get back in the race quick, they'll lose!
Meanwhile, Farmer Tyrone and Molasses slowly advance down the road toward the two mountains. Tyrone sings Keep Goin' Along, as he dances beside his donkey. By the end of the song, Jockey Pablo and Cowgirl Uniqua reach the top of the mountain.
Tyrone and his donkey, Molasses, pass the mountain and wave hello. Rembering the race, the horse riders slide down the mountain and get on to their horses. As Tyrone and Molasses appraoach the final stretch, Pablo and Uniqua ride their horses as fast as they can. They get closer and closer, with Austin announcing "This is still anybody's race!" As Tyrone reaches the finish line, Pablo and Uniqua run through, as Austin takes a picture. All three of the contestants seem to have won. Austin says it was a photo finish, so they don't know who won yet. As Austin views the snapshot, he discovers that the winner is Tyrone, who was ahead by a snout. Tyrone recieves a sparkling trophy and gives it to Molasses for all her hard work.
Uniqua's stomach growled so Tyrone invites everyone over to his house for blueberry muffins to celebrate. The Mississippi River transforms back into the backyard. The children sing the end song and enter Tyrone's home. Uniqua opens the previously closed door and shouts "Yee-ha!". The end credits for the episode begin.