The district added a new 3-story wing, cafeteria, and Gym as well as renovating the existing building.

The stadium has been fitted with a turf field, an all-weather track, and improvements to the visitors' team's stands.

The current spot of the Bunnell School has been made into a faculty parking area.

Every morning, after the first block, teachers turn on their TVs for South Side Live, a student broadcast generally about 10 minutes long.

They have played every year since 1945, and starting in 1952—with a few exceptions—the teams have met on Thanksgiving morning is what is known as the Turkey Day Game.

If the winner is away, they walk home with a police escort through the other team's town, a tradition that began in 1967.

The school regularly sends several students to PMEA District Chorus, Band, and Orchestra festivals.

In order to be eligible, a student must be enrolled in the regular Chorus class and audition successfully for a spot.

They also are evaluated at adjudications and participated in Music in the Parks at Hersheypark in 2009 and 2011, both times winning best overall high school choir with a superior rating.

East Stroudsburg South has several clubs that compete against other schools, including FBLA and DECA.

[12] In 2010, one of the Reading Olympics teams placed first at the regional competition at Easton Area High School.

In 2011, the Mock Trial team placed first at the Monroe County Bar Association Invitational.