In the fall of 1820, Hannie Van Brunt has resigned herself to the fact that she will likely never marry. But when new schoolmaster Gideon Webb comes to Sleepy Hollow, Hannie wonders if her life might turn out differently after all. Caught up in solving the mystery of what really happened to Ichabod Crane so long ago, Hannie and Gideon soon find themselves caught up in another kind of mystery altogether-a growing love for each other!

Today, disenchanted investment banker Tess McIntosh returns home to help run Sleepy Hollow's locally famous soup shop. When Tess's grandmother and her friends are scammed, Granny asks Riley O'Toole to help Tess find the identity of the swindlers. Riley and Tess have a history-but thanks to one savvy granny, do they also have a future?