Catholic Charities of Maryland, the state’s largest private provider of human services, needed to reconsider its beloved Basilica holiday fundraising concert during the height of COVID-19. In place of an in-person gathering, we reimagined the experience as a digital “Advent-style” calendar—inviting families across Maryland to rediscover the season from home. Each day of December revealed a new activity within themes like music, cooking, crafts, reflections, and games, offering simple ways for households to pause, create, and celebrate together. Playful holiday illustrations and a joyful campaign identity carried across a multimedia awareness effort—from transit ads and social media to an animated commercial—building anticipation around each day’s surprise. The concept also attracted major sponsors including McCormick and Domino Sugar, whose products were incorporated into the cooking experiences throughout the calendar. The initiative not only gave the community a shared moment of warmth during a season of isolation, it surpassed the fundraising performance of the previous in-person event and returned for two additional holiday seasons, establishing a new tradition of comfort and joy across Maryland.