She frequents folk festivals across the nation, such, as the Falcon Ridge Folk Festival in Hillsdale, New York. She has also toured with the likes of Mary Chapin Carpenter, Patty Griffin, Ani DiFranco, The Nields, and Shawn Colvin.
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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.
Williams's first full album, The Honesty Room, was recorded on her own label, called Burning Field Music. The album was soon picked up by Waterbug Records. In 1995, she moved to Razor & Tie, which re-released the album. Williams has released five more solo albums to date on the Razor & Tie label.
In 1998, Williams formed the short-lived group Cry Cry Cry with Richard Shindell and Lucy Kaplansky. After releasing an album composed mainly of folk cover songs in 1998, the group toured from 1998 to 2000.
As a songwriter, Williams says that she can't stand cliches and chooses instead to "dig deeper" into the meanings of things and find their inner beauty. She ignores the cultural icons of our time and chooses instead to celebrate "the real heroes" in our lives: the song "Are You Out There," for example, commends her favorite disc jockeys for helping her stave off her teenage loneliness by playing music she could relate to.
Williams has long maintained in interviews that she wants her music to be an "efficient career," and something she can do her entire life. The way she strives to accomplish this is to "continuously court your muse; to keep writing stuff that feels risky about things you believe in, that you're really feeling."
Williams has also tried to give something back to her community, founding organizations like the Snowden Environmental Trust and taking part in many benefit concerts. One notable example of this is a show at Alcatraz with the Indigo Girls, to benefit prisoner-rights group Bread and Roses.
While Williams writes songs that often touch upon her own past, she maintains that she hates "journal entry songs" and prefers to write for others. As a result, fans know precious little about her personal life. For years fans have argued over the question of Dar's sexual orientation; songs like "Iowa" and "The Blessings" have been said to be hinting at encounters with female lovers. After a magazine said she was bisexual, she said that she had been misquoted and was actually straight, although she added that she would have preferred to have "stayed ambiguous ... for the sake of solidarity" and so that all fans could relate easily to her music.  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.
- The nickname "Dar" has erroneously been thought to relate to the Daughters of the American Revolution, which is mentioned in the song "Flinty Kind of Woman." However, it actually originated due to a mispronunciation of "Dorothy" by one of Williams's sisters.
- Williams is a vegetarian and allergic to dairy. As someone who has toured a great deal of the time and had trouble finding suitable dining on the road, Williams was inspired to co-author and publish a directory of natural food stores and restaurants called The Tofu Tollbooth in 1998.
- While writing songs for her album The Green World, Williams incorporated her ongoing interest in religion into the process. One particular inspiration was the book Drawing Down the Moon by Margot Adler.
- I Have No History (1990 – rare demo tape)
- All My Heroes are Dead (1991 – rare demo tape)
- The Honesty Room (1993)
- Mortal City (1996)
- End of The Summer (1997)
- Cry, Cry, Cry (1998 as Cry Cry Cry)
- The Green World (2000)
- Out There Live (2001)
- The Beauty of the Rain (2003)
- The Tofu Tollbooth (1998, co-author)
- Amelee (2004 expected release)