After losing her husband the previous year, Erin takes her children, Ava Grace, twelve, and Hunter, seven, and fun-loving Grandma Ruth to visit relatives up north for Christmas. She hopes distractions will spare them from another season of holiday grief. However, when Grandma Ruth runs into Kyle, Erin's childhood sweetheart, and learns he's heading in the same direction, she secretly invites him to ride along.
At first, Erin isn't pleased about Grandma Ruth's holiday surprise. After all, Kyle was the one who broke up with her. But, when Grandma Ruth pulls out the Christmas Car Bingo, and Kyle agrees to play along with the kids, Erin is reminded of the good times the two of them had as teenagers causing her feelings toward him to soften.
When Hunter wins the bingo prize from Grandma Ruth, a Victorian village figurine, he explains to Kyle that his father set them up for him during the Christmas holidays. Each day a new one was put out and it was up to Hunter to guess which one was new.
As the road trip continues, every place they stop, (welcome center, gas station, diner) Hunter mysteriously finds another figurine. Erin, Kyle, Ava Grace, and Grandma Ruth begin wondering who is leaving them for Hunter to find. Each suspecting the other. But, Hunter believes they are signs from his father because he is an angel now and can do magical things.
After so many stops, at Hunter's request, they run behind schedule and Kyle suggests taking shortcuts off the main highway. When Erin finally agrees, they get lost and during their argument, she accidentally runs over something causing a flat tire on a snowy highway miles from a town. Kyle offers to go for help and when he returns in a horse-driven sleigh, he tells them about a town up ahead that he knows Hunter will want to see. As they reach the town, Hunter is in awe. It's a Christmas Victorian village come to life.
But, the excitement quickly fades for Erin when the hotel clerk turns out to be a former girlfriend of Kyle's who reminds her that he is not the settling down type. However, after Hunter runs off in the village, upset that his mom and Kyle appear to no longer be getting along, Erin is grateful when Kyle eventually finds him. What began as an awkward holiday road trip rekindles a romance with a touch of Christmas magic along the way.