Cindy Cashdollar was 13 when the Woodstock Festival changed everything in 1969. “Actually, my family was renting in Phoenicia. We were building a new house, and I went into Woodstock just to see who was coming in. I remember it was very crowded and a lot of people looking very wild with bed rolls.”
The idea that she might end up playing steel guitar with everyone from Bob Dylan to Van Morrison was the furthest thing from her mind.
“I remember seeing Jimi Hendrix sitting in a parked car somewhere on Tinker St., but mother would not let me – of course, I was on lockdown that weekend. I had older friends, and they were all there, and my mom was certain I was gonna run away and go to the festival. And that’s actually what I was thinking of doing. I was on high alert.”
A member of a family that’s third generation Woodstock residents, she was always around music, but she never even thought of doing it for a living. “The Cashdollar name is a very old name in the Woodstock area. The women farm The Locust Grove Dairy, and my father Roger Cashdollar not only worked the dairy but delivered milk to the Woodstock area. I didn’t want to (play music) for a living. I just loved playing. I found it a very relaxing thing.
“The concerts here (in Woodstock) were called Sound-Outs, and they were really to me kind of the precursor to the Woodstock Festival. I went to a couple of those when I was around 13. My friend’s father would drop us off there, and it was Cat Mother and the All-Night News Boys and Paul Butterfield. So, I saw a lot of music here at a very young age, and when I was about 13 I started going out to clubs and saw a lot of great music.”
Cindy Cashdollar has worked with Rod Stewart, Ryan Adams, Asleep At The Wheel, Albert Lee, Marcia Ball, Rory Block, Jorma Kaukonen, and Leon Redbone – to name a few. She is currently on tour with Sonny Landreth. But she was already in her 20s when she decided to make music her career.
“In the late ’70s I was in an all-female band called Whiskey Before Breakfast with Jennifer Condos on bass. Jennifer went on to play with Stevie Nicks and Sheryl Crow and a bunch of people and it was fun, but I still wasn’t thinking about doing it for a living.
“I think that’s when I started playing in a bluegrass band, then later with Rick Danko and Levon Helm. They had an acoustic thing going on for a while. You could actually make some money. And as low as the money was back then, it made more sense even though I wasn’t making a lot of money. Financially you could still have a car and maintain an apartment and be ok. So, that was around then. I would say it was the early ’80s that I started touring and doing this more for a living.
She’s done solo projects, but the vast majority of her playing has been as support to the headliner. Van Morrison is one of her favorites. ‘I think to me each person I work with brings something different even if it’s not like a strong energy. Something about the artistry and touring with Van Morrison. His band was amazing. A larger band, they’re incredible. His vocals still sound great.”
Morrison was one of the first concerts she went to. “I was still young at the first live show that I saw, I just felt like I just knew his music.
“I did Dylan’s sessions in Criteria Studios in Miami for his Time Out of Mind record. There was certainly trepidation meeting him the first time, but he couldn’t have been nicer, and he was just a joy to work with, and I think that was really about it. I find if you start thinking too much, then you get in your own way. So, I really think you just have to put the mindset, ‘Ok, I’m just here to work. I’m here to do my job, to back up the artist and serve the song the best I can.’ You just don’t let your mind wander sometimes. You do get in trouble now and then.”
Cindy took home five Grammys in the eight years she spent playing with the iconic western swing band Asleep at The Wheel, and when she had a car accident in Woodstock in 2017, the local newspaper ran a headline saying she’d been “asleep at the wheel.”
“What people didn’t know was the accident happened during the day, and I had just finished the tour and a week later got married. Then two days after I got married, I started rehearsals and went on the road again. It was on 209 which has curves. And I was nodding off. I just felt so exhausted, and the next thing I know I just woke up and saw trees and the car hitting something. The car flipped out and ended up flipping over and landing the opposite way. I was just so out of it. I thought the car was gonna blow up. I thought I had broken my back because the car was totaled. I was starting to get out the passenger side which I had to climb in a little Honda. It turned out to be a compression fracture, but I felt it in my back.”
Cindy is enjoying her current tour with Sonny Landreth. “When I play with him, I really feel like I know his stuff so well before actually starting to work with him, and it feels like we’re talking. It feels like two close friends doing a conversation is what it feels like to me. Only we’re playing, and it’s just nice not even thinking. It’s just music where we’re talking, and he’s such a phenomenal player.”
