For twenty-eight years, Hamilton MacDougall led the Choir, becoming much beloved with the young women who sang with him. After MacDougall’s retirement, Randall Thompson assumed the role of conductor from 1927-29, during which the Choir gave its first performance in New York City: a "Christmas Vespers" service in City Hall. In fact, he dedicated his double-choir motet "Pueri Hebraeorum" to the Choir. After Thompson’s time with the Choir, Lowell P. Beveridge oversaw the group in 1929-1930, followed by Maurice C. Kirkpatrick in 1930-1931. Edward Barry Greene then became the director from 1932-1940; afterwards, Margaret M. Winkler manned the podium from 1940-1948. From 1949-1953, Margaret Winker, Peter Waring, and Charles Reeve Shackford alternately directed the Choir. In 1953, William A. Herrmann, Jr. began a period of service to the Wellesley College Choir that would last over thirty years, during which important endowments to the Choir established two annual choirs: the Betty Edwards Dober '40 Memorial Concert, which first took place in 1964, and the Marjorie Copland Baum Concert that started ten years later in 1974. Following William Herrmann's retirement, director Constance DeFotis took the podium, and under her leadership, the Choir traveled overseas for the first time to perform several major works, including a new piece by composer William DeFotis. During DeFotis’ time, the Chamber Singers were established in 1988.
Under the direction of Susan Davenny Wyner from 1994-98, the Choir performed the Brahms Requiem with the Harvard Glee Club, as well as Robert Levin's new edition of the Mozart Requiem with the Virginia Glee Club and members of the Boston Baroque. In two trips to Europe, Wyner directed the young women in universally acclaimed performances at St. Peter’s Basilica and the American Academy of Rome in Italy in the spring of 1998. Later in the fall, Brian Clarence Hulse took over the position. Under Hulse, the Choir performed the Pergolesi Stabat Mater and the Weber Mass in G; toured New York City, Washington D.C., and Florida; and commissioned several pieces from Boston composers including Marjorie Merryman and Jonathan Bailey Holland. The Choir also had the opportunity to record East, West of the Sun, a major work for women's voices by Wellesley professor Arlene Zallman. During the Choir’s 100th Anniversary Season (2000-2001), in the tenure of director Vincent Metallo, the Choir sang a concert of French spiritual music including the Poulenc Litanies de la Vierge Noire. In the same year, the Choir also performed Haydn's Creation with the Glee Club of the U.S. Naval Academy.
In the Fall of 2001, the Choir welcomed its current conductor, Lisa Graham, to the podium. During her first year with the Choir, she led a performance of English folk music and a tour to Montreal, Quebec. Since this time, Choir has toured every year, domestically and internationally. In 2003, the voices of the Wellesley College Chamber Singers and Choir were featured in the motion picture Mona Lisa Smile, which was filmed on campus. Additionally, under Lisa Graham's direction the choir has commissioned important new works by William Hawley, Kirke Mechem, David Childs and Joan Szymko, Abbie Betinis, Augusta Read Thomas and Steven Sametz. Wellesley College is a charter member of the National Collegiate Choral Organization, of which Dr. Graham is a founding member, former vice-president, treasurer, and past-president.