On a cold December afternoon, a small cluster of students made their way from Baker Library to the Radcliffe Quadrangle. Donning mismatched coats and colorful scarves, their voices cutting through the cold Boston air as they sang Christmas carols, was the Harvard Holiday Caroling group, the university’s first student-led, cross-campus caroling event. 

The idea was brought to life by Benjamin T. Rossen ’23, and inspired by his own experiences. Although Rossen himself had never done traditional caroling, he recounted fond memories of singing Christmas carols with his family throughout his childhood. When he arrived at Harvard, he noticed that the campus lacked this tradition that brought students together. This absence prompted him to begin designing a caroling initiative of his own. 

“I want people to revel in the Christmas spirit,” Rossen shared. 

Rossen had long been involved in Harvard’s music community before the caroling event. As an undergraduate, he concentrated in Economics and Music before earning a master’s degree in piano performance through the Harvard–New England Conservatory dual-degree program. While pursuing his masters, he also served as Executive Director of Lowell House Opera. It was this latter role that equipped him with many of the skills that allowed him to lead this caroling group. “Being the Executive Director of an opera company forced me to be a salesperson,” Rossen noted. “It galvanized me to recruit people.” 

From that vision, Harvard Holiday Caroling took shape. Rossen designed the program as a moving performance: students would travel across Harvard’s campuses, from the Business School to the far corners of Harvard College, all while singing a variety of carols. For Rossen, the project was ultimately about bridging the invisible gaps across the university. 

“I felt that the college, the undergraduates, are a bit siloed from the graduate schools,” he explained. “Why not curate something like the caroling event and facilitate cross engagement between the schools?” 

The set list itself reflects this intention. Rossen combined traditional Christmas carols such as Deck the Halls and Silent Night, alongside secular hymns and selections that nodded to a range of cultural traditions. The group even performed songs in German and Spanish. 

Support for the idea grew quickly. After reaching out to the Office for the Arts, Rossen received institutional backing, including support from Dean Jason Meier and the DSO.  However, organizing the caroling wasn’t wrapped up in a perfect bow. “The ongoing challenge is the recruitment and marketing—just the visibility of the event,” he said. “I want people to understand the cost benefit of spending 30 minutes, or maybe a few hours… and then feeling that collective spirit.” 

On the day of the event, turnout was small, but the program unfolded just as intended. The group sang at high-traffic points across campus, drawing in listeners as they passed. Students paused their brisk walks, parents with young children lingered, and faculty stepped outside to listen. In the Quad, a window slid open as someone leaned out to catch a better view. After several songs, bystanders approached to offer their appreciation, with some calling out, “bravo!” 

As the group moved across campus, the sound drew new listeners–and singers–into its path. “It was a community event that grew larger as we went along,” caroler Ross Simmons ’21 said. Ian Kim ’28 heard the music while working on a Computer Science project. “It sounded very heavenly,” he shared. He left his work and ran outside as soon as he heard the caroling. 

“I was very delighted that we had people jump in who weren’t part of the core group,” Rossen said. “We had alums, undergraduates, visiting students, graduate students, and local Boston singers. It was a wonderful, eclectic mix.” 

When the group reached the Radcliffe Quadrangle, a shuttle bus pulled up only feet from the singers. Without breaking rhythm, they turned toward the driver and redirected their harmonies, later joking that the bus was “in B-flat.” During one song, the group slipped into exaggerated faux-Gaelic accents, exchanging smiles as they sang through the cold. The mood was light, playful, and unmistakably festive. 

Looking ahead, Rossen believes this event is only the beginning. He hopes to bring future performances to other areas of Harvard's extended campus, and build upon the joy even further.

“Ultimately, traditional caroling is going to people’s homes, knocking on doors and singing,” Rossen said. “I think we reached people without knocking — but in a similar way.”