October In New York is about chance meetings and the unconventional love affair of two people destined to be together. Gwendolyn North and Thomas Winslow meet late one night in New York City when they get stuck in an elevator at their hotel. After an hour alone with her, trapped between floors, the handsome, reserved businessman from Chicago is intrigued by the lovely, free-spirited artist from Massachusetts and invites her to have a drink with him in the lounge. The attraction between them grows stronger over the next six days, until a lie threatens to destroy any chance of a relationship. Both have been disappointed with love in the past. Unable to deny their feelings, they follow their hearts and face the obstacles of a seemingly futile romance.