Over Eaglebrook’s 104-year history, traditions and the art of shared experiences have been an integral part of what makes Eaglebrook truly shine as a community. Out of all the traditions, Country Fair stands, at least in my mind, as the highlight of the year —an event where all members of the community truly come together. Reminding us of old-school New England style fairs since the 1940s, Country Fair is an event that, regardless of weather or turnout, never fails to please students, parents, and faculty from around the world.
The first Eaglebrook Country Fair took much earlier. Students and advisors plan a week ahead of time, making posters, formulating ideas, and assigning shifts. As they go through this stage of planning, students are more than ready to welcome parents into their community the following week. Then, Friday finally arrives! October 17, 2025 place in 1942 and started as a parents’ Open House where students could invite their family for a weekend of fun and showcase their growth at the school. The students are responsible for showcasing their academic, athletic, and creative talents. Eighty years later, Country Fair still holds the same, if not more, enjoyment and pride, including a sprinkle of creativity from the students through their concession stands, which tends to be a bit different every year.
Country Fair takes place on the third Friday of October each year, but the fall spirit at Eaglebrook School starts After breakfast, students and parents gather in the Assembly Area. This is not always comfortable because the room is full of people. However, students are more than eager to offer their seats to parents, demonstrating just how much members of the Eaglebrook community appreciate one another. The President of the Student Council gives his Sixth Form assembly. Last year, Teddy Cashel ’25 gave his talk on the various ways perseverance changed his life. We are more than excited to see what words of wisdom our current president, Ryan Kang ’26, has for our community.
After the President’s Assembly, students and guests head to classes. Although short, students have the opportunity to showcase what they have learned to their parents in all their academic and elective courses. Following lunch, students and parents are welcome to connect with families, as well as have time to themselves and explore Eaglebrook, including the school’s archives, which opens in the afternoon.
Students and faculty gather to prepare their stands. Then, at 2:30, the Jazz Band offers an open-air performance on the gym steps. Then the booths open. Families go around Memorial Field to explore all of the food and challenges offered. Some personal highlights of mine include Ms. Lien’s Bubble Tea, Mr. Goodrow’s Yaki Soba, and Mr. Bogel’s hay bale obstacle course. The next day, parents have parentteacher conferences in the morning, and after another buffet lunch, go to the athletic fields to watch their child play a sport. After sports, students are free to go with their parents. Fall spirit and excitement are at an all-time high at Eaglebrook. Our community is eagerly looking forward to receiving this year’s guests during Country Fair 2025!
