York made her Broadway debut as Mallory in the musical City of Angels, and her performance won critical acclaim. After City of Angels, she has been in many performances on stage, including Fantine in Les Misérables, Irene St. Claire in Crucifer of Blood, The Younger Woman in Stephen Sondheim's Putting It Together (with Julie Andrews), which earned her a Drama Desk Award nomination, Norma Cassidy in Victor/Victoria (for which she won a Drama Desk Award), Marguerite in The Scarlet Pimpernel, Lili Vanessi/Katharine in Kiss Me, Kate, Reno Sweeney in Anything Goes, Dorothy in Summer of '42, Miss Fancy in Sly Fox, Ruth Sutton in Dessa Rose, earning her another nomination for a Drama Desk Award, Mother in Ragtime, Christine Colgate in Dirty Rotten Scoundrels, and in The Sound of Music as Elsa Shraeder at the Hollywood Bowl. She appeared as Guenevere in the National Tour of Camelot in the 2006-2007 season, for which she earned the Golden Icon Award from Travolta Family Entertainment for Best Actress in a Touring Production as well as the Carbonell Award. In 2009, she played Dolly Levi in the Reagle Music Theatre production of Hello, Dolly! in Waltham, Massachusetts and won an IRNE Award for her performance.