Cindy Cashdollar A Slide Guitarist Legend and Woodstock Native

By Michael Cobb | March 12, 2022

Inside+Out is thrilled to share our exclusive interview with five-time Grammy award-winning slide guitarist and Woodstock local Cindy Cashdollar. After living in Austin, Texas for 23 years Cashdollar returned home to Woodstock in 2015. When she’s not on tour, she enjoys the quiet beauty of the Hudson Valley and finds plenty to do on a local level. We caught up with Cashdollar to talk about living and working in Woodstock and her upcoming tour schedule.

One of the few true natives, Cindy Cashdollar (yes, that’s her real name) was born and raised in Woodstock. “My grandparents had the Locust Grove Dairy, and my dad delivered the milk to Woodstock and the surrounding areas,” she says. Cashdollar’s youth coincided with the arrival of Bob Dylan, who sought refuge from fame and a place to heal from a near-fatal motorcycle accident in the mid-60s. His band, soon to be dubbed “The Band”, followed as did many other musical legends of the 1960s like Van Morrison and Jimi Hendrix.

Thanks to the diverse programming of venues like the infamous and well-remembered Joyous Lake, Cashdollar grew up absorbing a wide variety of music. Seeing Van Morrison at the Woodstock Playhouse at age 12 was hugely inspirational. “Van was the first live show I’d ever been to. He was part of a benefit for local musician John Herald and his wife Kim, who had lost their house in a fire. There were other artists performing including Odetta, Happy and Artie Traum, and John Hammond Jr. It was life-changing to see all that at such a young age and to experience the energy between the performers and the audience. Recording and touring with Van later for his Keep It Simple Album was incredible,” she says.

Beginning on Dobro (a wood-bodied guitar with a steel resonator cone), soon she was working with bluegrass musicians such as John Herald, folk musicians Happy and Artie Traum, and other area acoustic acts. Cashdollar later took up lap steel, the electric equivalent, and played with bluesman Paul Butterfield, and Levon Helm and Rick Danko of The Band, when they were doing unplugged shows in the tri-state area. Her career continued to climb from the 80s onward, and since then Cashdollar has worked with the biggest names in American music including Leon Redbone, Willie Nelson, Merle Haggard, Dolly Parton, Asleep At The Wheel, Dave Alvin, Rod Stewart, Bob Dylan, Van Morrison, and many more.

For her tasteful work, Cashdollar is regarded as one of the top slide and steel guitar players in the USA and has won five Grammys. She was the first woman to be inducted into The Texas Steel Guitar Hall of Fame, has also been inducted into the Texas Music Hall of Fame, and has been a nominee for Instrumentalist of the Year by the Americana Music Association. In May 2022 she will be honored by the Country Music Hall Of Fame in an ongoing program called “Nashville Cats”, which recognizes musicians who have played an important role in the recording and touring industry. “Basically those of us that are side musicians, playing and creating music behind the artists,” she says.

Reflecting on her career trajectory, she says, “It’s always great to play with your heroes, and growing up here there were many.” Working with so many artists, Cashdollar says it’s challenging to pinpoint career highlights. “There were numerous special and interesting experiences,” she says. “Getting the phone call to play on Bob Dylan’s Time Out of Mind record was memorable, but each experience was and continues to be incredible. I love all kinds of music and getting to play so many different styles reminds me how great it is to do what I love to do.”

Though the pandemic curtailed much of her touring schedule, Cashdollar kept busy with recording projects at local studios. “I work a lot with engineer Dave Cook at Area 52 in Saugerties. The beauty of technology is that clients can send audio files to a studio, I record my parts onto the tracks, and they get them back later the same day no matter where they are,” she says. Thinking about artists she has yet to work with but would love to, she says, “John Oates (Hall and Oates) is a wonderful writer who, when not touring with Daryl Hall, also has been doing his acoustic Americana tour. I’d love to play with him.”

Currently, she is working with legendary English guitarist Albert Lee on a collaborative session and is looking forward to getting back on the road this spring. “In March, I’ll be touring with Sonny Landreth as a duo. He’s one of my slide guitar heroes. From March 25-27, I’m participating in “We’ve Got The Beat: Women in Music Summit” at the Bearsville Theater in Woodstock. There will be concerts, panels, screenings and discussions. I’ll be performing, as will Debra Devi, Joan Osborne, Darlene Love, and others. In addition to the musical artists, there are known filmmakers, radio personalities, producers, recording engineers and authors. There will be many opportunities for the public to interact during the Q & A discussions. It’s going to be a highly educational and motivational summit. But it’s not just for women, everyone is welcome to attend,” she says.

In June, Cashdollar will be giving a clinic on slide guitar at Camp Cripple Creek at the Full Moon Resort in Big Indian (about 30 min west of Woodstock). “It’s an incredible workshop that Jim Weider and The Weight Band run. It’s all about the music of The Band. People come from as far away as Australia and Japan to take songwriting and music workshops; it’s a gorgeous place. So there are lots of local things happening,” she says.

When she’s not touring or recording, Cashdollar enjoys going for walks in the area and taking drives to other counties. “No matter where you look it’s nice,” she says. “Because touring is just starting to pick up, I’ve had more time to see friends and family. It’s been a nice way to be local again.”

Inspired to give back to the local community, Cashdollar says, “I’m a member of the Catskill Animal Sanctuary, which rescues abused and abandoned farm animals. I love their work. It’s a charity close to my heart.” Cashdollar also helps musicians who struggle with issues of addiction. “I’m a music ambassador with Melia Clapton’s organization Turn Up For Recovery. They continue to put out music videos that feature many performers such as Derek Trucks and Susan Tedeschi, Robert Cray, Sheryl Crow and others to raise money and awareness for people who don’t have the financial means for a rehabilitation facility.”

Growing up in the Hudson Valley undoubtedly influenced Cashdollar as a musician and a person. She says, “Hearing so many different kinds of music in my teens here was like a soundtrack of early influences. Though there are fewer venues today, what we have is great. There’s The Falcon, The Colony, and The Bearsville Theater. We have an abundance of musicians and artists, so in that way, it’s the same as it’s always been. Woodstock and the Hudson Valley continue to be great places to live, work and create. It’s got the creative mojo.”

Above all, Cashdollar is looking forward to playing again both on national tours and on a local level. “One of the projects I enjoyed doing pre-pandemic was called ‘Cindy Cashdollar and The Syncopators’ which includes my brother Russell on drums. The recently departed and greatly missed Tony Falco really encouraged me to put my own group together. We do jazz, swing, rockabilly, everything danceable. We were playing monthly at The Falcon and had an incredible crowd of swing dancers. I really miss that and am looking forward to people feeling safe enough to do it again, hopefully, this summer at The Falcon.”