In early December 2019, Darien High School's Model Congress delegation attended the annual Yale Model Congress weekend, the oldest student-run organization in the nation, which was formed to foster an appreciation for American democracy in high school students.

The DHS delegation was successful, in terms of the awards ceremony and attitude. Several delegates won awards. Tripp Lyons and Henry Kanlian received Best Delegate awards, Peter McLean and Mike Mercein won Best Legislation, and Christian DaSilva accepted an Honorable Mention for his role as Secretary of State in the Presidential Cabinet. As a small delegation of 10 people, the group was considered for a Small Delegation Award, which Darien High has won three times in the past.