At the age of 8, his younger sister (Katie Shore from Asleep at the Wheel) started taking fiddle lessons and this quickly piqued Ross’s interest to learn the instrument for himself.

Additionally, his background and training as a member of the Texas Boys Choir was Holmes first exposure as a touring musician across the U.S.[4] Holmes has worked with famous bands and artists such as Mumford & Sons, Nitty Gritty Dirt Band, Bruce Hornsby and the Noisemakers, Warren Haynes, Ryan Bingham, Bela Fleck, Abigail Washburn, and Keith & Kristyn Getty.

Cadillac Sky formed in 2002 when Holmes met founding members Bryan Simpson (vocals, mandolin), Matt Menefee (banjo) in Texas.

He toured globally as the band evolved to one of the largest pop sensations, making headline appearances for 250,000 people at the Glastonbury Festival, Lollapalooza in Chicago, and Red Rocks Amphitheatre.

[7] Holmes joined Railroad Revival Tour, a multi-day jaunt that Mumford & Sons, Edward Sharpe and the Magnetic Zeros and Old Crow Medicine Show traveled by a 14-car train from Oakland to New Orleans, playing six concerts along the way.

A documentary called Big Easy Express developed out of this tour, directed by Emmett Malloy premiered at SXSW 2012 and won a Grammy Award in 2013.

On October 23, 2018, Holmes self-released his debut album, "Not Very Good at Winning," a collection of 12 Texas-style contest fiddle tunes recorded in 360° sound at Southern Ground Studios in Nashville, Tennessee.