Anderson Hall is Brewster's premiere performance facility and it is where many school assemblies take place throughout the year. Together the main floor and balcony offer seating for approximately 500. The Hall is home to a proscenium theater with an in-ceiling acoustical reflector panel that offers superb sound projection throughout the Hall. Eight microphones placed throughout the Hall with control access from the balcony are used for recording performances or live broadcasts. World-wide video conferencing and dedicated telecommunications features are accessible directly from the stage podium.

Anderson Hall is the home stage for Brewster's HOWL chorus, Chamber Orchestra, Wind Ensemble, and Jazz Band. Brewster students studying the technical aspects of theater have the opportunity to assist and master the direction of sound, lighting, and broadcasting features within the Hall. It is also the performance venue for the faculty and students of the Heifetz International Music Institute, which is in residence at Brewster Academy each summer.

Performers who have entertained audiences in Anderson Hall include internationally acclaimed violinist Daniel Heifetz, renowned fiddlers Natalie MacMaster and Donnell Leahy, and musician Cas Haley of "America's Got Talent." In July 2008, National Public Radio's "From the Top" program was broadcast live from Anderson Hall.