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Riley Thomas (Abigail Hawk) is a rising star at one of the world's most noted holding companies. With Christmas fast approaching, she is sent to the small town of Chestnut, Vermont to evaluate the assets of one of their companies, an outerwear clothing manufacturer. As she begins making plans for liquidation, she hires the company's founder, Nick (Howard Hesseman)-now retired-as her apprentice to help. Of course, everyone assumes she's there to save the company and she keeps her true motives a secret. In the process, she comes to appreciate what the company means to the small town; and she falls in love with its youthful CEO, Wyatt (David O'Donnell). She slowly comes to embrace the small town's values and even helps create a new product line just in time for Christmas. As her priorities change and her love grows, will Riley be able to stand up to her boss, Preston Bullock (Chevy Chase) and save the company she was supposed to destroy?