Grandparents and grandchildren that live apart often rely on communication technologies, such as messengers, video conferencing, and phone calls for maintaining relationships. While some of these systems are challenging for grandparents, others are less engaging for children. To facilitate communication, we developed StoryBox, a tangible device that allows sharing photos, tangible artifacts, and audio recordings of everyday life. We conducted a preliminary study with two families to identify design issues, and further refine the prototype. Subsequently, we conducted a field study with four families for up to four weeks to better understand real-world use and examine inter-generational connectedness. We found that StoryBox was accessible, simple, and helped bridge the technological gap between grandparents and grandchildren. Children communicated asynchronously in a playful and idiosyncratic manner, and grandparents shared past family memories. We provide insights on how to ease communication between different generations, engage them in sharing activities, and strengthen family relationships.