The Yale Westchester Alumni Association plays a special role as impresario of Yale music in Westchester. It began with the formation of a Music Committee consisting of many Yale alumni who fit into the music world. Undergraduate musicians, alumni musicians, graduates of the Yale School of Music, and others were combined into a group which considered many ways to draft musical interchanges between Yale and Westchester. The first event in 2000 was the creation of the Millennium Musicale, an event in the home of a Scarsdale resident that drew on two Yale founts of talent, the School of Music and Yale a cappella singing groups. A violinist and pianist from the Yale School of Music gave a concert in a private home, and their concerti was followed by two a cappella singing groups, the New Blue and the Yale Alley Cats. Many local merchants contributed food and drink, and the event was a landmark success, trumpeted nationally by the Association of Yale Alumni out of New Haven.  

Subsequently, more Yale musicians were tapped to contribute to the Scholarship Banquet in 2000, including the Yale Whiffenpoofs, Yale’s original a cappella group, the oldest collegiate a cappella singing group in the world, founded in 1909. Others included a gifted pianist from the Yale School of Music and a soprano, Regina Possavino of Crestwood, who previously had benefited for four years from the financial aid program of TWAA. 

With the success of these two programs under their belt, Yale Westchester alumni took off their gloves and let music flow. The Yale Glee Club had performed at the Hitchcock Presbyterian Church in Scarsdale in 1995, and again in 1997, with a strong turnout from Yale alumni and local audiences. In 2001, the Yale Glee Club was the central piece in a series of celebrations that honored Yale’s tercentennial. Held at the Grace Church in White Plains, followed by a reception at the Westchester Arts Council spaces at 31 Mamaroneck Avenue in White Plains, the event was attended by over 350 people who included Yale alumni and civic leaders who wished to recognize and honor this Yale event in Westchester.             

Since that time, Yale-created music has flowed into Westchester at an increasing pace. Subsequent musicales have enlarged the roles of the Yale School of Music, and the professional musicians it trains, at that graduate level. In 2002, the Yale Musicale in Westchester included several faculty, student performers and performing alumni of the Yale School of Music, including Dean Robert Blocker, as well as an undergraduate a cappella group. 

Other musicales, banquets and regional gatherings have seen performances by opera singers, the Yale Opera, violinists, cellists, pianists and many student a cappella groups, including the Yale Whiffenpoofs, Whim N Rhythm (senior women), the New Blue, Something Extra, Yale Alley Cats, Yale Spizzwinks, and Redhot and Blue (co-ed). Taken together with Broadway musicals (Oklahoma and La Boheme), and subsequent banquets and musicales, Yale Westchester Alumni Association has developed a special place worldwide among Yale alumni associations as a place for music. With the exception of the Yale Club of New York City and Yale University itself, with its native Yale Club of New Haven, it is doubtful that any regional Yale association comes close to Yale Westchester Alumni Association as a resource for music.  

One has the feeling that the YWAA’s recent years of music, augmented by its members’ attendance at Caramoor, the Performing Arts Center and the Westchester Philharmonic, only scratches the surface. Yale alumni include a cappella singers who are reviving their groups as alumni, including the Yale Whiffenpoofs of New York, the Yale Alley Cats and the Yale Spizzwinks. Additionally, many Yale alumni are active in Broadway shows as musicians. A recent discovery of families who are happy to host musical events in their own homes has further strengthened the launch pad for new musical events from Yale and from among Yale alumni.  

Many students select Yale not because it has the best law school or best science or best English department, although an argument could be made to support each thesis. Many students who want to be doctors or lawyers or scientists choose Yale because it is uniquely infected with music at all levels. Hobbyists and professionals equally enjoy the musical ambience and spirit of Yale music. Therefore, the effort to engage alumni and Yale performing groups in musical events in Westchester is notably easy.