It's been a year since Debbie's smash hit "Wonderland." Now living in a small town, she's found true love and left the music industry behind to teach kids the value of their own musical talents. But when her manager begins to pull her back into the limelight to celebrate the 20th anniversary of her first single, "Out of the Blue," Debbie has to decide which will come first – music or love?

Resort developer Madison Lane is tasked with finding a location for a new ski resort. Her boss tells her to take a trip to Christmas, Colorado, to consider the location. On her way into town, Madison has a minor fender-bender with the town’s welcome sign. Town Sheriff Gage McBride gives Madison a ride into town so she can attend her meeting with the mayor while the car is towed and repaired. Little does Madison know that the town is on a mission to convince Madison that Christmas is the best place for the new ski resort.