Wee Sing characters Punchinello, Sillywhim, Little Bunny Foo Foo, Weeber, Snoodle and Doodle, and Trunky (originally Tusky) who are all from earlier Wee Sing Videos, ride the Wee Sing Train to Singalingaland where Singaling (voiced by Mikey Moran) and Warbly (voiced by Maureen Robinson) are hosting a big musical party called "The Wee Sing Festival". Singalingaland also happens to be an extension of Tim and Annie’s game board, Wee Singdom. However, the main guest of honor (a singing rainbow) is missing, so as each character performs his or her respective performance, Chug-a-Long the engine and Cubby the caboose are sent to go look for her by asking a cirrus, stratus, cumulus cloud where she disappeared too. Eventually, she is found after Tim and Annie find her playing with their cat friend, Staccato, and as a reward, Chug-a-long and Cubby invited Annie and Tim and Staccato to attend the Wee Sing Festival, and Singing Rainbow is able to perform.

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