World traveler Tracy Bennett agrees to extend her stay in Waverly Lake beyond summer in the hopes of affording her girlfriends' trip—a three-month excursion in New Zealand! And well, Aunt Dee could use her help at Woodsman's Lodge, packing away summer items and prepping for the winter holiday crowd. So, she's stuck until Thanksgiving. Meanwhile, Ben Walker is drawn back to Waverly Lake after the death of the custodian to his parents' estate. He plans to work at Aunt Dee's for his stay and is surprised to learn his childhood best friend Tracy is also working at the lodge. Hesitant to tell anyone else in Waverly Lake who he truly is for fear the town will want him to fill his parents' shoes, he gives a false name and pretends not to know Tracy. While Tracy's questioning of the mysterious Ben escalates, Aunt Dorothy assigns them to her pet project—Lovetoberfest. The October event is set to match guests on three blind dates around town. Tracy and Ben are forced to test run and narrow down five proposed dates to the best three. As the two reluctantly go on match-making practice full of apple orchards, corn mazes, and acorn painting, Tracy can't help but be attracted to Ben. Their chemistry makes her question not only her trip overseas but her long-term future; yet she can't shake the feeling he's hiding something. Ben's (re)connection with Tracy is undeniable, and while the dates push them closer, he's running out of time to face his tragic past and tell Tracy they're not, in fact, strangers at all.