Excited about the Fall Fair, the Ponysitters are busy with a multitude of preparations. The Fair also brings out a competitive nature in some of the contestants, but nothing works better than teamwork. Unfortunately, Isabella will be in her native Brazil during the Fair, but she helps Skye out before she leaves. This is Skye’s first year competing in the Obstacle Challenge with her horse. The other Ponysitters do whatever they can to help her train, so she feels confident enough to ride. She faces another challenging obstacle of her own, her dyslexia, and she struggles but tries her best to fill out the necessary entry forms to compete. Shelby is also competing, and although she is a more seasoned rider, Skye feels confident that she can beat Shelby and win. While Skye practices for the Obstacle Challenge, Olivia is judging the Animal Showcase. Convinced she will win, Bianca is disappointed when she finds out everyone gets a ribbon. Meanwhile, Kyle is training a guide dog. Just like every year, Grandpa enters the pie-making contest along with his rival, George. This year, Ethan has also entered. Unfortunately, their rivalry reaches new heights and gets the best of George and Grandpa until they realize that the only way to have something presentable for the competition is to work together. Although there are many unexpected challenges, avoidable blunders and bruised feelings at this year’s Fall Fair, teamwork, selflessness, and positive thinking prevail.