Captain Jake and the Never Land Pirates Adventures of The Little Engine That Could (2011)

In DreamLand, Little E. wakes the control tower and the other dream hauler engines up, so she can start work while also dreaming of being a dream hauler. She comes by the birthday train, which consists of a locomotive named "Red E. #35" and a wagon containing a female clown named "Beverly", a toy soldier named "Major", a toy plane who can fly named "Ace", a ballerina doll named "Jillian", two stuffed giraffes named "Lou and Bud" and a sock monkey named "Hudson". After finding the Caboose for it, Little E. attempts to follow it to the real world, but she is stopped by the Tower. Little E. then tries to pull several boxcars to Big L., but she ends up causing traffic for the other engines with the Tower reminding her that she is supposed to pull one boxcar at a time due to her small size. Little E. gets a little help from Rusty L., who is an old and wise engine.

In the real world, a boy named Richard shows his friend Marcus, his grandfather's watch. Two bullies named Scott and Stretch throw a snowball at Richard, which makes him slip and hand the watch over to them. He is worried that his dad would be unhappy that he lost the watch. Marcus tries to help him, but Richard does not want help from him at all. Richard decides to take a walk in the park, but trips over some train tracks he has never noticed before and find a train nearby. He boards one of its cars to take shelter from the cold, unaware that it is pulled by Rusty (who is sleeping on the job again) and suddenly wakes him up. He immediately returns to DreamLand (with the tracks appearing at the front and disappearing at the back of him) with Richard inside. While passing through the tunnel to DreamLand, the tunnel collapses, trapping Richard and the trains in DreamLand while the junction goes crazy. After Rusty informs the others what happened, Richard climbs out and is confused and scared by the talking trains. The Tower realizes that Richard's presence in DreamLand has damaged the dream-reality continuum and can only be fixed if Richard is returned to the real world. She sends some of the engines to dig out the tunnel and is forced to demote Rusty to a track-cleaner (in which he accepts the consequences), much to Little E's dismay. She then offers to take Richard home on the rumored tracks that lead over the mountain. The Tower, looking for a way to preoccupy Little E. and Richard while the other trains try to do the important work of clearing the tunnel, agrees, sending them both on their way while also promising to give Rusty his job back afterwards and even throw him a Ticker-Tape Parade. While searching for the track, they find themselves being chased by the Evening Express, who can't slow down to avoid hitting them. Richard, who suddenly believes that he is dreaming, tries to fly but ends up falling on the Evening Express. He manages to get back on Little E. but they are pushed off the track by the Evening Express. After rolling through the hills, they manage to get back on the tracks. They suddenly find the birthday train, which had derailed when the tunnel collapses. Little E. decides to take the train to the real world herself and attempts to get information from the other engines about the old track, but they don't believe the track even exists. Little E., Richard, and the toys decide to find the track themselves.

Little E. manages to finds the track leading up the mountain. Along the way, they come across an old bridge that partly collapses when trying to cross it. Richard nearby falls off but is saved by Little E. and Ace. They use an old cargo hook pole as a makeshift rail for the bridge to get across. Later, they enter a dark area in the mountain and while climbing up a hill, Little E. runs out of water due to a leak in her water tank, causing the train to roll backward until Richard manages to stop it by applying Little E.'s brakes. A black engine appears and offers to take them back to the real world for her. She agrees but he suddenly reveals himself as the Nightmare Train, an evil, nightmarish, locomotive who can create nightmares and plans to use Richard as a means to send nightmares to the real world and leaves after derailing Little E. and the birthday train. In the Nightmare Train, Richard is confronted by illusions of the bullies but the others encourage him to stand up to them. Ace escapes and goes to help Little E. After refilling her tank using water from a nearby water tower, she and the Caboose find themselves still unable to get back on the track. Little E. sees another stretch of tracks below and drops down the cliff, successful landing back on the tracks. Meanwhile, Richard escapes and falls off the train after a failed attempt to uncouple the cars. Little E. finds him and they quickly chase down the Nightmare Train. While confronting him, the toys sneak out while Little E., Richard, and Ace trick him into speeding down a side-track at rapid speed. Major then uses his badge to plug the leak in Little E.'s tank (as well as admitting his feelings to Jillian) and they continue their way up the mountain. They eventually make it to the top and travel through a portal that leads them to the real world, where no time has passed at all.

Little E. returns to DreamLand, tells her story about her trip over the mountain, and is promoted to a dream hauler as a reward for her bravery while Rusty gets his job back. Once back, Richard has gained the confidence to confront the bullies and get his watch back and the bullies are caught by the principle, who is annoyed that they aren't in detention. During the credits, the following photos are shown: Richard showing his watch to his class, the toys with their new owners, the Nightmare Train defeated and derailed on a snow bank, Rusty's Ticker-Tape Parade, and lastly, Little E. taking more trains through the mountain.

Trivia

 * The Little Engine That Could was released on DVD in 2011 the same year when Jake and The Never Land Pirates aired on Disney Junior.