Williams was born in Mount Kisco, New York, and grew up in Chappaqua with two older sisters, Meredith and Julie. In interviews, she has described her parents as "liberal and loving" people who early on encouraged a career in songwriting. Williams began playing the guitar at age nine and wrote her first song two years later. However, she was far more interested in drama at the time, and majored in theater and religion at Wesleyan University.

Williams moved to Boston, Massachusetts in 1990 to further explore a career in theater. She quickly became stage manager of the Opera Company of Boston, but on the side began to write songs, record demo tapes, and take voice lessons. Her voice teacher pushed her to try her hand at performing at coffeehouses, but due to the intimidating nature of the Boston folk music scene, as well as her own battles with stage fright, things got off to a rocky start. In 1993 Williams moved to Northampton, Massachusetts.

Early in Williams's music career, she opened for Joan Baez, who would make her relatively well known by recording some of her songs. Her growing popularity has since relied heavily on community coffeehouses, public radio, and an extensive fan base on the Internet. In recent years, she has performed on nationwide television shows such as Late Night with Conan O'Brien.

Williams recorded her first full album, The Honesty Room under her own label, Burning Field Music. The album was soon picked up by Waterbug Records. In 1995, she moved to Razor & Tie, and her first album for that label, 1996's Mortal City received substantial notice, given that its release coincided with her tour with Baez. With that success, Razor & Tie re-released The Honesty Room. By the time of her third release, End of the Summer (1997), Williams' career had gathered substantial momentum, and the album did remarkably well, given its genre and independent label status.

In 1998, Williams, Richard Shindell and Lucy Kaplansky formed the group Cry Cry Cry as a way to pay homage to some of their favorite folk artists. The band released an eponymous album of covers and toured from 1998 to 2000.

She has since released three more studio albums on the Razor & Tie label (The Green World (2000), The Beauty of the Rain (2003), and My Better Self (2005)), as well as a live album (Out There Live (2001)).

Williams has lent her talents to support various causes, founding the Snowden Environmental Trust and taking part in many benefit concerts. For example, she performed in a show at Alcatraz with Baez and the Indigo Girls, to benefit the prisoner-rights group Bread and Roses.

On May 4, 2002, she married Michael Robinson, an old friend from her college. Their son Stephen Gray Robinson was born on April 24, 2004. She currently resides in Rhinebeck, New York.

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