Middle School students enjoy many activities specific to the Middle School. In recognition that Pennington students have a variety of interests, activities are varied and include academics, community service, the arts, and social opportunities. Students are encouraged to try a variety of activities and learn where their talents lie.

Those students seeking unique intellectual opportunities can participate in Odyssey of the Mind, an international educational program that provides students with creative problem-solving opportunities. Pennington middle schoolers work together to solve problems that range from building mechanical devices to interpreting literary classics in creative ways. Students have the opportunity to participate in competitions on the local, state, and world level. Middle School students can also get involved with Mathcounts, a program that builds math skills, promotes logical thinking, and strengthens students’ analytical abilities. “Mathletes” are coached in everything from basic arithmetic skills to math logic, probability, statistics, linear algebra, and polynomials. Students compete as a team in Mathcounts competitions against other schools.

The Middle School Student Council meets every other week to plan social activities and community service projects. Student Council representatives are elected in each grade and work to promote school spirit and a stronger sense of community. The entire Middle School participates in a Community Service Day in the fall and the spring, participating in service projects both on and off campus. Becoming part of the Campus Guide group is another way Middle School students can help the community. In addition, Middle School students can join Upper School students in such community service activities as the annual Crop Walk, the HomeFront Holiday Dinner, and tutoring in Trenton.

Middle School students interested in the performing arts have an opportunity to take part in the Middle School spring play as actors and actresses as well as stage technicians. In addition, the Middle School chorus performs at assemblies and special programs during the year. Students who play a musical instrument may participate in an ensemble, while those who wish to learn to play an instrument may sign up for private music lessons.

Social opportunities are also important to Middle School students. Each year there are several Middle School dance parties, complete with themes, decorations, food, and a deejay. Several swim-basketball parties, where students can swim, play basketball, listen to music, or do all three, take place prior to vacations. The final social event of the year for Middle School students is Countdown, an evening of friendly competition, swimming, and food.