Cindy Cashdollar is an American musician specializing in steel guitar and Dobro. She grew up in Woodstock, New York, where she perfected her skills by playing with bluegrass musician John Herald, blues musicians Paul Butterfield, and Levon Helm and Rick Danko of The Band. After residing in Austin, Texas, for 23 years, she has now returned to her native Woodstock, New York. From 2005 to 2008, Cashdollar played with Elana James, Redd Volkaert (and, sometimes, Nate Rowe), as The High Flyers, appearing on A Prairie Home Companion twice, as well as playing Austin area venues.