Tom and his sister Judy come home from school and are thrilled to start Christmas vacation! (“Prologue/Now is the Time”). Tom can’t wait for all his presents, but Mom, Dad, and Judy remind him this is also a time for giving to others. Still, Tom begs his parents to let him open one gift early. Although there are still several days until Christmas, Mom and Dad relent and let them open “just one.” To Tom’s delight, he gets a pair of Jolly Ramblers ice skates.

After almost forgetting to thank his parents, Tom heads out to practice with his new skates (“Brand Spankin’ New”). Tom’s friends, Annie and Rachel, invite him to come skate with them (“Extraordinary Day (Part 1)”). They run into Ralph, who has a the “hottest new model” of skates, Club House Skates. Tom’s pride is wounded. Ralph is about to join them in skating (“Extraordinary Day (Part 2)”) when Tom decides to go home. Tom throws his skates on the ground as his friend Harvey passes, admiring the new skates.

When he gets home, Tom asks Mom to open another gift because his skates weren’t impressive enough (“Unfair”). Mom refuses, leaving Tom to sulk.

On Christmas Eve, Tom is still moping around. To get him out of the house, Mom sends him on an errand to get butter. At the store, Harvey is working and helps Tom get what he needs. During Christmas vacation, he works part time for some extra money. Harvey excitedly shows Tom two dolls he found in the stock room. Although they’re broken, his sisters will love getting them for Christmas (“Lots of Care”). He asks Tom to hide them at his house so he can surprise his sisters.

Tom can’t shake off wanting the best skates. He decides if he can find enough paid work, he can save up money to buy the Club House Skates. Tom does various tasks for neighbors (“The Work Song”). As he’s working at the store where Harvey works, Mrs. Patton, the owner, tells Tom that Harvey’s mom is sick. He needs to work to support the family while she’s recovering. Humbled, Tom realizes he has been approaching Christmas the wrong way (“Now is the Time (Reprise 1)”). Tom asks Mrs. Patton to help him with shopping for some Christmas surprises.

At home, Tom gets Dad, Mom, and Judy to help repair the dolls for Harvey’s sisters (“A Christmas Mission”). Tom reveals that he bought the Club House Skates – for Harvey.

When Tom shows Harvey the dolls and skates, Harvey is so touched (“Now is the Time (Reprise 2)”). Tom returns home, ready to celebrate Christmas with his family (“Finale”).