The Winston School San Antonio offers a variety of enrichment activities and extracurricular clubs for our students. Club offerings are dynamic and may vary from year to year, depending on student interest and participation.
As a member of the Texas Association of Independent Athletic Organizations (TAIAO) and the Independent Schools Association of the Southwest (ISAS), Winston students compete annually in academic and art competitions with other students from around the state.
These enrichment activities include:

The National Beta Club is a non-profit organization that recognizes and encourages academic achievement, leadership, character, and service in students from grades 6–12*. The club's motto is "Let Us Lead by Serving Others". The club's graduating 12th graders receive a diploma seal to symbolize their membership. The club offers opportunities for students to participate in building activities, and engage in community service.

The National Honor Society (NHS) is an organization that recognizes high school students who excel in scholarship, leadership, service, and character. The NHS was founded in 1921 and has chapters in all 50 states, US Territories, Canada, and around the world. More than just an honor roll, NHS serves to recognize those students who have demonstrated excellence in the areas of scholarship, service, leadership, and character. NHS members wear a specific stole to signify their membership during the graduation ceremony.

Dungeons & Dragons (D&D) Club provides Winston Upper School students an opportunity to learn and play the game of Dungeon & Dragons. D&D offers numerous educational benefits, particularly in developing social-emotional learning (SEL) skills, communication, critical thinking, and problem-solving.

Freedom Arts Magazine is the creative brainchild of founding student editor Robert Hook, a member of the graduating class of 2012. Robert’s inspiration and tenacity were the essential ingredients in bringing forth a literary magazine that the Winston community both enjoys and treasures. Freedom Arts is published annually and showcases the creative talents of Winston's students.

Rotary EarlyAct provides Lower School students a glimpse into the work of our Rotary Interact Club (see next listing). EarlyAct is based on the principles of Interact, modified so that they are age-appropriate, and offers service and outreach opportunities for Winston’s youngest students.

Sponsored by the North Central Rotary Club and the Boerne Sunrise Rotary Club, Rotary Interact offers Winston students an opportunity to create greater understanding and promote goodwill with youth around the world. Interact meets twice a month and functions similarly to a regular Rotary Club.

The Winston Maker Space Club provides an opportunity for students (3rd to 12th Grades) to engineer, build, and 3D print their designs as well as construct computer boards capable of basic and advanced functions and participate in Computer eSports.

Student Council serves the student body in a variety of ways. The purpose is to promote good citizenship among the students, assist in the management of student concerns, and provide purposeful direction of school activities.
Esports club provides a structured environment for students to compete in video games, similar to traditional sports teams. The club offer opportunities for students to develop valuable skills like teamwork, communication, and problem-solving, while also fostering a sense of community and belonging.
Chess club members learn, practice, and play chess, fostering both social and intellectual development. It offers a space for players of all skill levels to improve, socialize, and potentially compete in friendly matches or tournaments.
Girl Scouts explore, discover, and lead. Participants develop essential skills like goal-setting, decision-making, and teamwork through badges, activities, and community service. This organization develops girls of courage, confidence, and character who make the world a better place. Join for fun, friendship, and leadership development.
Gradening club focuses on cultivating plants, fostering environmental awareness, and promoting healthy eating habits. These clubs typically involve hands-on activities like planting, maintaining, and harvesting from the school gardens, while also exploring related topics like soil health, pest control, and sustainable gardening practices.