Alan built a castle in rural Illinois with his late love Adrianne. Facing life alone, he revisits their fantasy through musical reenactments transporting him to the world they shared.

Clio befriends Fred, a homeless former jazz singer down on his luck. They form a special bond over music, and Clio, having just lost her own father, helps Fred reconnect with his own daughter, just in time for Christmas.

Felicity's ornament scavenger hunt could save her family's toy store, but first, she must get the heartbroken city alderman on board with her plan.