The ride, which has become part of the events surrounding the Academy of Country Music awards, preceded a 7-hour concert at downtown Las Vegas' Fremont Street Experience.
"It's really, really unbelievable how much it's grown. We're just glad to be very much a part of it and just glad to see all the riders join in," Montgomery said.
He said the academy asked the singing duo Montgomery Gentry to kick off the ride four years ago, and drew about 36 bikes. This year, more than 600 people pre-registered, and a steady stream of walk-ups on Sunday expected to push the number well above 1,000.
Riders paid a minimum of $30 (22 EUR) to take part. Proceeds go to the academy's charitable fund.
The academy has raised more than $1.5 million (1.1 million EUR) for charities and organizations around the world. Its foundation was established for programs dedicated to the awareness, growth and education of music.
"It's impressive that these amazing people and fellow artists donate their time and money for such a worthy cause and charity," Gentry said. "I'm flattered to say I'm involved."
Craig Morgan and Richie McDonald also rode in the event.
Montgomery Gentry, Morgan and McDonald are among the nominees for the 42nd annual awards presentation Tuesday evening at the MGM Grand and televised on CBS.