Cindy Cashdollar given Key to the Woodstock

Ray Benson, of Asleep at the Wheel, looks on as Bill McKenna and Rennie Cantine present the Key to the City to Cindy Cashdollar. (Photo by Jim Rice)

It was quite a surprise for Cindy Cashdollar when, during the June 30 show at Levon Helm Studios, where the splendid slide and steel guitar player was performing with Asleep at the Wheel, Woodstock Town Supervisor Bill McKenna and Rennie Cantine appeared on the stage and presented her with the Key To The City.  

“She had no knowledge of it,” said McKenna. “Asleep graciously allowed us to do it in the middle of their show…She’s actually the first one (to receive the honor) born and raised in Woodstock…The Key to the City is an honor, Woodstock honoring its artists.”


McKenna explained that there exists some sort of intermittently convening committee that meets “every couple of years, and nominates an artist to receive the award. It started in 2004 with Levon Helm, then it was the Traum brothers (Happy, and his late brother Artie, who received the award posthumously). Cindy’s brought our music across the country and played with countless musicians, including Asleep at the Wheel. It was particularly sweet to present her with it in Levon’s home,” said McKenna. 

Cashdollar, a descendant of Albert Cashdollar, a town supervisor from 1932 to 1943, and whose family ran the Locust Grove Dairy Farm, was indeed surprised. “I had no idea. I thought they were just doing a nice thing for Asleep’s 50th anniversary.” She had previously toured with the band for years, while living in Austin, Texas, but moved back home to Woodstock several years ago. “It was so nice. I thought it was really cool. I’m very happy to be part of the occasion. It was my second gig with the Wheel in god knows how many years. That coupled with playing at the Barn made it even more special.” 

The Key to the City is constructed by Cantine. “Rennie made this beautiful case,” said Cashdollar. “It was just like the Grammys, you pose with it backstage and then they take it away from you and the real one gets sent do you. And I was given some beautiful flowers from the barn. I felt like Queen for a Night.”

Asked what she might do with the Key to the City, Cashdollar replied “I’m going to find all the skeletons and open all the closets…”