Charlie Dickinson ’26 started at Harley in kindergarten, following her older sister Frances ’23. Ask how her family discovered Harley, and she tells a story about her mother seeing a group of Harley students out one evening—maybe heading to prom—struck by how polite, kind, and respectful they were to one another and everyone around them. Afterward, she said simply, “I want my kids to go to Harley.”
Along the way, a number of teachers shaped Charlie’s path. Raj “Mr. S” Singaravelu (Lower School, 2004-07; Middle School History, 2007-present) brought warmth and fun to the classroom. Bill Schara (History, 1997-2021, 2022-23) had a profound impact in her freshman year, introducing a style of learning that felt more like college than high school. Rather than asking students to take notes, he pushed them to notice what interested them, reflect on their takeaways, and fully engage. It was in his classroom, Charlie says, that she first truly experienced Harley’s Joy In Learning.
She credits Kristin Sheridan (Upper School History, 2007-present) with a kind of grounded clarity—someone who could make any challenge feel manageable. And then there is Doug Gilbert ’87, P ’21, ’24, ’27 (Middle School History, 1999-present), whose endless store of historical knowledge has become family lore; Charlie and her sister still toss out “Gilbert Fact Knowledge” at random moments. Fittingly, these favorite teachers all taught history, helping inspire Charlie’s plan to major in political science.
Leadership has been another defining thread of her Harley experience. Her student council journey began with disappointment after losing a run for class president in eighth grade. But the loss taught her something lasting. Someone told her, “You can win if you know you’re the best person for the job.” At the time, that felt too bold for someone naturally modest.
That changed. From freshman class vice president to sophomore representative-at-large, junior year secretary, and now student council president, Charlie has grown alongside the role. She even explored the idea in a grade ten paper for Dave O’Brien P ’19 (English, 2011-present), writing, “Modesty is the tool of the patriarchy.” Student Council, she says, gave her confidence and reshaped how she sees leadership, not as checking boxes, but as showing up every day, setting an example, and serving a community. The experience has also deepened her respect for governance and public service.
Her leadership extends beyond the classroom. In track and field, Charlie earned all-state honors this year, finishing sixth in the 1500-meter Race Walk at the New York State championships and breaking her own school record with a time of 7:37.04. She also competed at Nike Nationals, adding another milestone to a remarkable senior year.
Next fall, Charlie will head to Middlebury College to study political science, carrying with her the intellectual curiosity Harley has helped cultivate. Though she considered attending college abroad, she decided she wants to be part of change in the United States, not run from its challenges. Middlebury appealed to her for its international perspective, strong study abroad opportunities, and engaged student body. She is especially eager to explore perspectives beyond her own—including what she calls “middle America”—to better understand different cultural mindsets and communities.
That curiosity, paired with conviction, feels quintessentially Charlie. Whether in the classroom, on the track, or in student government, she has approached Harley not just as a place to excel, but as a place to engage deeply with ideas, with people, and with the world she hopes to help shape.
