Judy Whitfield, a beloved singer-songwriter who not only performed her own songs at area venues since 1990 but also organized community and arts gatherings, passed away at her home from complications of MS on January 16.
Judy booked and hosted the acclaimed Women in Music series at the Tinker Street Café from March 1993 through 1994, which featured such artists as Bar Scott, Ellen McIlwaine, and Janine Pommy Vega. Her 2009 Music at the Movies series at the Tinker Street Cinema included artists like Jules Shear and Tracy Bonham. She also conducted songwriting workshops for adults as well as school children at Woodstock and Phoenicia elementary schools.
A self-described “Air Force Brat,” Judy was born on November 20, 1949, and grew up in far-flung places including Alaska, England, and Southern California. She began writing songs at 19 and taught herself to play guitar, woodshedding and forming the folk-rock band Four Roses in San Francisco while she worked at the legendary Boarding House, where Steve Martin, Robin Williams and others got their start. There, she also met fledgling sound engineer/future producer Julie Last, with whom she reconnected in New York City in 1977 after both women happened to move East. While Julie was working as an assistant engineer at the Record Plant Recording Studios, she arranged for Judy to get a job there as a receptionist where she became a beloved welcomer to many famous rock musicians of the day.
Meanwhile, Judy formed a succession of NYC-based bands for which she wrote songs and sang, including Cheap Date, Rake’s Progress, the Millionaires, and eventually the Judy Whitfield Band. They performed at the legendary CBGB, Trax, the Bitter End, and Kenny’s Castaways, among other venues. As a singer-songwriter, she performed at the Bluebird Café in Nashville, the Iguana Café in L.A.; Café Sin-é and the Knitting Factory in New York City. She also wrote songs for artists ranging from Penny Arcade and Maria Manhattan to the Peter Healey Dance Company, as well as collaborating on songs with Cheryl Poivier of Kid Creole and the Coconuts. In her artist bio, showing her characteristic humor, she wrote that she’d worked with “the greats, the near-greats, and the ingrates.”
In 1990, Judy moved to her Woodstock home, where she began performing as a singer-songwriter accompanying herself on acoustic guitar on stages with John Herald, Spider Barbour, Paul McMahon, and other local luminaries at the Bearsville Theater, the Colony, and numerous area venues. Her blend of pop, folk, and country wowed audiences with her memorable songcraft that presented piercing portraits of a gallery of characters and striking images. She recorded a six-song EP, Point of No Return, which Billboard magazine described as “a sophisticated and intelligent blend of pop music.” In 1995, the Woodstock Times’ “Werewolves of Woodstock” column awarded her Women in Music series as the region’s “Best Ongoing Music Series,” with Judy being named “Ms. Entertainment.”
After being diagnosed with multiple sclerosis in 1998, Judy continued to perform, including stints in Oaxaca, Mexico, and in western Ireland. Several of her songs became music videos, now available on YouTube. She forged numerous friendships along the way and enjoyed hosting pals at her charming streamside cottage on Wittenberg Road. Her love of music and art, her curiosity, generosity, and her wit and humor made her a truly loved Woodstocker.
On “Judy Day,” June 11, following the 5 p.m. interment of her ashes at the Woodstock Artists Cemetery, we will celebrate her life well-lived with musical performances, spoken remembrances, her recorded music, and photography and videos.
A Celebration of the Life of Judy Whitfield (1949-2025) will be held Wednesday, June 11 at Colony Woodstock, 22 Rock City Road.
Doors Open at 6 p.m. Musical and spoken tributes from 7-10 p.m.
Performers and speakers will include Sylvia Bullet, Paul McMahon, Brian Hollander, Penny Arcade, Julie Last, Robert Burke Warren, Tim Moore, Tim Kapeluck and more.
Donations will be accepted in Judy’s memory for the Woodstock Library’s upcoming Woodstock Music Archives.
— Holly George-Warren
Join the family! 
