Charlie "Chopper" Gilmore

Charlie grew up on a grain and livestock farm in Northwest Iowa, where he developed a deep appreciation for life and freedom. His passion for motorcycles ignited in the early 1960s when he, his brother Slider (a Sturgis Hall of Fame member), and Tator (a twin-engine drag racing champion) got their first Harleys. Over the past 60 years, Charlie has ridden countless miles across the U.S., Europe, Alaska, and to the Sturgis Rally every year.

A graduate of South Dakota State University with a degree in Agriculture, Charlie is also a U.S. Army veteran. He served as a combat platoon leader with the 101st Airborne in Vietnam. While stationed at Fort Benning, he began honing his skills in repairing and restoring Harleys—a passion fully supported by his wife, Toni.

Charlie is a founding member of ABATE of Iowa’s District 8, an ordained minister, and a former National Chaplain for the Sons of Silence. He is a familiar face at motorcycle conventions and a tireless advocate for motorcyclists’ rights. His powerful “Price of Freedom” presentation is legendary within the community.

As a skilled builder and restorer, Charlie has created twin-engine choppers displayed in the U.S., Germany, and Sweden, and has restored hundreds of motorcycles featured in museums—including the Sturgis Motorcycle Museum. He also served as a pit crew member for his brother’s championship drag racing team and now supports his nephew, Cody Gilmore, a former motocross racer competing in Harley Bagger Pro racing.

Charlie’s contributions have earned him numerous honors, including the Motorcycle Riders Foundation’s John “Farmer” Eggers Award (2010) and the NCOM Silver Spoke Award (2022). He truly embodies the spirit of freedom and unwavering dedication to the motorcycle community.