In Train Yard of Dream Land, Little Engine is a shunter who dreams of becoming a Dream Hauler and bringing dreams to the Real World. She tries to pull boxcars for Big Locomotive, but ends up causing traffic for the other engines, and the Tower reminds her she is only supposed to pull one boxcar at a time due to her small size. Little Engine later gets encouragement from Old Rusty, an old and wise engine.
In the Real World, a boy named Richard is antagonized by two bullies, Scott and Stretch, who steal his grandfather's pocket watch. Richard flees to the park, where he encounters a train and takes shelter in it. Rusty, who is pulling the train, is unaware he's inside and returns to Dream Land with him. Richard's presence in Dream Land causes the tunnel to collapse, trapping him and the trains in Dream Land. The Tower sends some engines to start digging out the tunnel and is forced to demote Rusty to a track-cleaner, much to Little Engine's dismay. Upon learning from Rusty about the old tracks that go over Dream Mountain to the Real World, Little Engine offers to take Richard back to the Real World in exchange for Rusty getting his job back and the Tower agrees.
While heading towards Dream Mountain, Little Engine and Richard are chased by the Evening Express, who cannot slow down to avoid hitting them. They are knocked down to the hills, but manage to get back onto the tracks. After passing through the Mushroom Forest and a prairie, they find the birthday train, which had derailed when the tunnel collapsed, so Little Engine takes the train to the tunnel herself and attempts to get the other big engines to take the train on the old tracks, but the engines do not believe the tracks exist, so Little Engine, Richard and the toys decide to go themselves.
Upon finding the tracks, they start up the mountain, and encounter an old, rickety wooden bridge that partly collapses as they are crossing it. Richard almost falls off, but is saved by Little Engine and Ace the Jet Plane, and they finish crossing by using an old Railway Mail pole as a makeshift rail for the bridge. Later that evening, Little Engine runs out of water due to a leak in her water tank, causing her to roll downhill until Richard and Hudson the Sock Monkey apply her emergency brake.
Just then, a black engine appears and offers to take Little Engine's friends to the Real World. She agrees, but he then reveals himself as the Nightmare Train, an evil locomotive who can create nightmares and plans to use Richard to send nightmares to the Real World. Aboard the Nightmare Train, Richard is confronted by hallucinations of the bullies, but is encouraged to stand up to them. Ace escapes and goes to help Little Engine after refilling her tank using water from a nearby water tower. Meanwhile, Richard falls off the Nightmare Train, and reunites with Little Engine. They chase down the Nightmare Train, retrieve the others, and continue up the mountain after fixing the leak in her tank. Little Engine struggles as they near the top, but Little Engine perseveres and reaches the portal to the Real World, and after delivering all the toys they stop at Richard's school and find that no time has passed.
Richard gains the confidence to stand up to the bullies and reclaim his grandfather's watch from them, and afterwards they get in trouble with the principal and go to detention. Richard reconciles with his friend Marcus, who is proud of him for getting his watch back and decides to keep his adventure in Dream Land a secret. Meanwhile, Little Engine returns to Dream Land through the restored tunnel and is promoted to being a Dream Hauler as a reward for her accomplishments, and Rusty gets his job back and a Ticker tape parade as well. During the closing credits, the toys are shown with their new owners in the Real World, while the Nightmare Train is derailed on a snow bank.
Voice cast
Alyson Stoner as Little Engine, a little steam Shunter engine who dreams of being a Dream Hauler and becomes close friends with Richard.
Whoopi Goldberg as the Tower, a control tower who is in charge of everyone in the train yard.
Patrick Warburton as Caboose, a red caboose who is part of the birthday train.
Jeff Bennett as Red Engine, the red #35 Dream Hauler.
Bennett also voices Hudson, a green and white sock monkey with a British accent who serves as the vice leader of the toys and Little Engine's fireman.
Mocean Melvin as Big Locomotive, a silver streamlined Dream Hauler with purple and orange stripes.
Jim Cummings as Rusty, a senior Dream Hauler and friend to Little Engine.
Cummings also voices the Evening Express, a white streamlined Dream Hauler who pulls a fast express.
Rodney Saulsberry as Big Freight Engine, a green and orange Dream Hauler who hauls heavy freight trains.
Saulsberry also voices Bud, a toy giraffe. He is much less talkative compared to Lou and does not speak until near the end of the film.
Brenda Song as Shiny Passenger Train, a yellow Dream Hauler who is very full of herself. She is one of many who was sent to help dig out the tunnel.
Chelsea Erinne Evered as Linda[dubious – discuss], a pink and white diesel engine who gives Rusty a broom-plow in place of his cowcatcher and gives it back at the end of the film.
Ray Porter as the Nightmare Train, a black experimental[original research?] steam engine with power over nightmares.
Dominic Scott Kay as Richard, a boy who wanders into Dream Land when Rusty accidentally falls asleep on the job, ripping a hole in the dream-reality continuum.
Michael Rodrigo and Luke Williams as Scott and Stretch, a pair of bullies who antagonize Richard in the real world.
Jamie Lee Curtis as Bev, a female clown toy who serves as the leader of the toys and Little Engine's engineer.
Charlie Schlatter as Major, a toy soldier who sometimes finishes his sentences with "sir". He gives up his badge to help bandage a leak in Little Engine's water tank.
Jodi Benson as Jillian, a ballerina doll who dances when she is happy.
Corbin Bleu as Lou, a toy giraffe who forms a duo with Bud.
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