​The longest Harley-Davidson ride ever recorded is attributed to Dave Barr, an American veteran and motorcyclist. In 1994, Barr set a world record by riding a Harley-Davidson motorcycle 83,000 miles around the world, including a 13,000-mile segment from the Atlantic to the Pacific across Northern Europe and Siberia. Remarkably, Barr accomplished this feat despite being a double amputee, having lost both legs in a land-mine explosion during his military service. His motorcycle from this journey is currently on display at the AMA Motorcycle Hall of Fame in Pickerington, Ohio .

Another notable long-distance Harley-Davidson rider is Dave Zien, a former Wisconsin state senator. Zien rode over one million miles on his 1991 Harley-Davidson Sport Glide, a testament to the motorcycle's durability and his dedication to long-distance riding. His achievement is recognized as the highest mileage recorded on a Harley-Davidson motorcycle .

In terms of endurance riding, Carl Reese set a record in 2017 for the longest distance ridden on a motorcycle in 24 hours, covering 2,116.5 miles. While the specific make of the motorcycle used by Reese isn't detailed in the available sources, his accomplishment showcases the possibilities of long-distance motorcycle endurance .

These riders exemplify the spirit of endurance and the capabilities of Harley-Davidson motorcycles in long-distance journeys.