Michel won the award for her creation of an inclusive drama program that invites students from all walks of life to contribute to performances by writing plays, directing, and expressing themselves freely onstage.

In the aftermath of the "Unite the Right" rally turned riot in Charlottesville in 2017, the students in theater at Monticello High School wrote and performed one-act plays addressing racial inequality.

In the spring of 2006, biology teacher Jeremy Dove was recognized with the Presidential Award for Excellence in Mathematics and Science Teaching.

[citation needed] Monticello High School offers 25 interscholastic sports as well as theater, scholastic bowl, and debate programs.

Barnes resigned in September 2014, after admitting to being involved with David Deane, the Vice President of Downtown Athletic, and Charles Phillips, the Vice President of Sales for Team Distributor, a sports apparel retailer in Maryland, in a scheme to fix bids on athletic apparel purchased for Monticello High School.

Four Monticello teams have won VHSL state championships - Football, 2007; Girls Swim & Dive, 2021; Boys Indoor Track & Field, 2021; eSports League of Legends, 2022.